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Heterocyclic Compounds

Heterocyclic compounds are a class of compounds that consist of carbon atoms and non-carbon atoms altogether forming a cyclic skeletal structure. These non-carbon atoms are collectively referred to as a heteroatom. The common heteroatoms include nitrogen, oxygen, and sulfur. Lactones, lactams, cyclic ethers that we’ve already learned are heterocyclic compounds. With similar properties of congeneric open-chain compounds, they will be discussed in corresponding chapters. This chapter will mainly discuss heterocyclic compounds with relatively stable ring system and with a certain degree of aromaticity, also known as aromatic heterocyclic compound.

There are many kinds and a large number of heterocyclic compounds widely distributed in nature. Many natural heterocyclic compounds in animals and plants play an important physiological role in the body. For example, heterocyclic structure exists in chlorophyll in plants, hemoglobin in animal blood, alkaloids and glycosides as the active ingredient in herbs, some antibiotics and vitamins, certain composition of amino acids in protein and bases in nucleotide. About half of the existing medicines have heterocyclic structures. Thus, heterocyclic compounds play an important role in organic compounds especially in organic medicines.

The most common and also the most important heterocyclic compounds are that with five-membered or six-membered heterocyclic ring and their fused heterocyclic compounds. Therefore, according to the size of the ring, heterocyclic compounds can be divided into five-membered compounds and six-membered heterocyclic compounds. E.g., furan, thiophene, pyrrole, imidazole, triazole and their fused heterocyclic compounds, indole, benzimidazole and diphenylene-oxide are all five-membered heterocyclic compounds, while pyridine, pyrimidine and their fused heterocyclic compounds, quinoline and quinazoline are all six-membered heterocyclic compounds.

According to the number of hetero atoms, five-membered compounds and six-membered heterocyclic compounds can be divided into one-hetero-atom-containing heterocyclic compounds and two-hetero-atom-containing and several-hetero-atom-containing heterocyclic compounds. E.g., furan, thiophene, pyridine, indole, quinoline, dibenzofuran, etc. are one-hetero-atom-containing heterocyclic compounds; imidazole, pyrimidine, benzimidazole, quinazoline, etc. are two-hetero-atom-containing heterocyclic compounds; purine, comprising more than two hetero atoms, is a several-hetero-atom-containing heterocyclic compound. According to the form of the ring in the molecule, heterocyclic compounds can be divided into single-heterocyclic compounds and fused heterocyclic compounds. E.g., furan, pyridine, pyrimidine, imidazole, etc. are single-heterocyclic compounds and indole, quinoline, dibenzofuran, purines, etc. are fused heterocyclic compounds.

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Structure Chemical Name CAS MF
3-Bromo-5-chloroimidazo[1,2-a]pyridine 3-Bromo-5-chloroimidazo[1,2-a]pyridine 1260656-94-7 C7H4BrClN2
9-[1,1'-Biphenyl]-3-yl-9'-[1,1'-biphenyl]-4-yl-3,3'-bi-9H-carbazole 9-[1,1'-Biphenyl]-3-yl-9'-[1,1'-biphenyl]-4-yl-3,3'-bi-9H-carbazole 1643479-47-3 C48H32N2
N,N-Dimethyl-phosphoramidochloridic acid [(2S,6R)-6-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-4-(triphenylmethyl)-2-morpholinyl]methyl ester N,N-Dimethyl-phosphoramidochloridic acid [(2S,6R)-6-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-4-(triphenylmethyl)-2-morpholinyl]methyl ester 956139-30-3 C31H34ClN4O5P
6-chloro-1,3-dihydro-5-iodo-2H-Imidazo[4,5-b]pyridine-2-thione 6-chloro-1,3-dihydro-5-iodo-2H-Imidazo[4,5-b]pyridine-2-thione 1394373-25-1 C6H3ClIN3S
1-bromo-4-(trifluoromethyl)cyclohexane 1-bromo-4-(trifluoromethyl)cyclohexane 30129-20-5 C7H10BrF3
5-Trifluoromethyl-imidazo[1,2-a]pyridine-2-carbaldehyde 5-Trifluoromethyl-imidazo[1,2-a]pyridine-2-carbaldehyde 881841-26-5 C9H5F3N2O
Morpholine,4,4'-(phenylphosphinylidene)bis- (9CI) Morpholine,4,4'-(phenylphosphinylidene)bis- (9CI) 37624-67-2 C14H21N2O3P
5-(3-Nitrophenyl)-1-[3-(trifluoromethyl)phenyl]-1H-imidazole-2-thiol 5-(3-Nitrophenyl)-1-[3-(trifluoromethyl)phenyl]-1H-imidazole-2-thiol 1105189-24-9 C16H10F3N3O2S
ETHOXYLATED METHYL GLUCOSIDE DIOLEATE ETHOXYLATED METHYL GLUCOSIDE DIOLEATE 86893-19-8 (C2H4O)n(C2H4O)nC43H78O8
Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I) Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I) 852445-88-6 C23H32AuClN2
1-(2-chloropyrimidin-4-yl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 1-(2-chloropyrimidin-4-yl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 1835668-75-1 C12H9ClN4O
1,1'-(benzene-1,4-diyldimethylene)-bis(3,5-dimethyl-1H-pyrazole) 1,1'-(benzene-1,4-diyldimethylene)-bis(3,5-dimethyl-1H-pyrazole) 172606-22-3 C18H22N4
Methyl 2-oxindole-4-carboxylate Methyl 2-oxindole-4-carboxylate 90924-46-2 C10H9NO3
ETHYL 5-AMINO-1-(TERT-BUTYL)-1H-IMIDAZOLE-4-CARBOXYLATE ETHYL 5-AMINO-1-(TERT-BUTYL)-1H-IMIDAZOLE-4-CARBOXYLATE 76182-23-5 C10H17N3O2
2-CHLORO-4-BENZYLAMINO-5-METHYLPYRIMIDINE 2-CHLORO-4-BENZYLAMINO-5-METHYLPYRIMIDINE 91396-13-3 C12H12ClN3
(R)-5-AMINOMETHYL-PYRROLIDIN-2-ONE (R)-5-AMINOMETHYL-PYRROLIDIN-2-ONE 173336-98-6 C5H10N2O
4-bromothieno[3,2-d]pyrimidine 4-bromothieno[3,2-d]pyrimidine 16285-70-4 C6H3BrN2S
4-Bromo-5-methyl-1H-pyrazol-3-amine 4-Bromo-5-methyl-1H-pyrazol-3-amine 1780-72-9 C4H6BrN3
1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione 206055-67-6 C11H14N2O6
3-IODO-6-METHYL-IMIDAZO[1,2-A]PYRIDINE 3-IODO-6-METHYL-IMIDAZO[1,2-A]PYRIDINE 885276-23-3 C8H7IN2
5-Methoxyindole 5-Methoxyindole 1006-94-6 C9H9NO
2-(4-CHLORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE 2-(4-CHLORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE 38922-74-6 C13H9ClN2
3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE 3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE 87630-36-2 C13H24BrNSi
1-[(4-Nitrophenyl)methyl]pyrazole 1-[(4-Nitrophenyl)methyl]pyrazole 110525-57-0 C10H9N3O2
3,5-Diamino-1H-pyrazole 3,5-Diamino-1H-pyrazole 16082-33-0 C3H6N4
5-(CHLOROMETHYL)PYRIDINE-2-CARBALDEHYDE 5-(CHLOROMETHYL)PYRIDINE-2-CARBALDEHYDE 754920-10-0 C7H6ClNO
5-Fluorothiophene-2-carbonitrile 5-Fluorothiophene-2-carbonitrile 32415-91-1 C5H2FNS
2,4-DICHLORO-7-IODO-5H-PYRROLO[3,2-D]PYRIMIDINE 2,4-DICHLORO-7-IODO-5H-PYRROLO[3,2-D]PYRIMIDINE 928840-99-7 C6H2Cl2IN3
3-CHLOROMETHYL-PYRROLIDINE 3-CHLOROMETHYL-PYRROLIDINE 876509-14-7 C5H10ClN
2,6-DICHLORO-N-METHYL-4-PYRIMIDINAMINE 2,6-DICHLORO-N-METHYL-4-PYRIMIDINAMINE 32998-03-1 C5H5Cl2N3
[4-(2-AMINO-ETHYL)-PHENYL]-CARBAMIC ACID TERT-BUTYL ESTER [4-(2-AMINO-ETHYL)-PHENYL]-CARBAMIC ACID TERT-BUTYL ESTER 457631-44-6 C13H20N2O2
N-BOC-3-BROMO-4-HYDROXY-PYRROLIDINE N-BOC-3-BROMO-4-HYDROXY-PYRROLIDINE 1017782-17-0 C9H16BrNO3
6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol 6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol 7400-06-8 C10H17N3O3
1H-pyrazole, 4-iodo-1,3-dimethyl- 1H-pyrazole, 4-iodo-1,3-dimethyl- 6647-97-8 C5H7IN2
1H-Imidazol-4-ylmethylamine dihydrochloride 1H-Imidazol-4-ylmethylamine dihydrochloride 72631-80-2 C4H9Cl2N3
tert-butyl azetidin-3-ylmethyl(methyl)carbamate tert-butyl azetidin-3-ylmethyl(methyl)carbamate 1053655-53-0 C10H20N2O2
1-tert-Butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1-tert-Butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1256359-15-5 C13H23BN2O2
N-(Furan-2-ylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine N-(Furan-2-ylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine 1218790-00-1 C15H20BN3O3
3-bromo-6-methoxyimidazo[1,2-a]pyridine 3-bromo-6-methoxyimidazo[1,2-a]pyridine 1044733-59-6 C8H7BrN2O
6-methyl-1H-benzimidazol-7-amine(SALTDATA: FREE) 6-methyl-1H-benzimidazol-7-amine(SALTDATA: FREE) 935873-39-5 C8H9N3
5-(3-fluorophenyl)pyridine-3-carbonitrile 5-(3-fluorophenyl)pyridine-3-carbonitrile 1214373-90-6 C12H7FN2
5-(forMylaMino)-1H-pyrazole-4-carboxaMide 5-(forMylaMino)-1H-pyrazole-4-carboxaMide 22407-20-1 C5H6N4O2
2-AMino-1,4,5,6-tetrahydropyriMidine Hydrochloride 2-AMino-1,4,5,6-tetrahydropyriMidine Hydrochloride 26893-39-0 C4H10ClN3
1H-IMidazole, 4,5-dihydro-2-(4-Methylphenyl)- 1H-IMidazole, 4,5-dihydro-2-(4-Methylphenyl)- 13623-58-0 C10H12N2
(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile 1146629-84-6 C17H26BN3O2
2,3-Bis(benzyloxy)pyridine 2,3-Bis(benzyloxy)pyridine 1228665-98-2 C19H17NO2
6-Chloro-5-nitroimidazo[2,1-b][1,3]thiazole 6-Chloro-5-nitroimidazo[2,1-b][1,3]thiazole 23576-89-8 C5H2ClN3O2S
4-CHLORO-3H-IMIDAZO[4,5-C]PYRIDINE 4-CHLORO-3H-IMIDAZO[4,5-C]PYRIDINE 81053-66-9 C6H4ClN3
4-BROMO-6-FLUORO (1H)INDAZOLE 4-BROMO-6-FLUORO (1H)INDAZOLE 885520-35-4 C7H4BrFN2
1-tert-butyl-5-chloro-1H-pyrazole-4-carbonitrile 1-tert-butyl-5-chloro-1H-pyrazole-4-carbonitrile 1050619-87-8 C8H10ClN3
Pd(IPr)(acac)Cl Pd(IPr)(acac)Cl 868705-03-7 C32H43ClN2O2Pd
1-(DiMethylsulfaMoyl)pyrazole 1-(DiMethylsulfaMoyl)pyrazole 133228-21-4 C5H9N3O2S
S-2-(CBZ-AMINOMETHYL)PYRROLIDINE-HCl S-2-(CBZ-AMINOMETHYL)PYRROLIDINE-HCl 1033245-45-2 C13H19ClN2O2
6-BroMo-2-chloro-8-fluoroquinazoline 6-BroMo-2-chloro-8-fluoroquinazoline 953039-25-3 C8H3BrClFN2
(3R,5R)-5-Methylpyrrolidin-3-ol hydrochloride (3R,5R)-5-Methylpyrrolidin-3-ol hydrochloride 857651-11-7 C5H12ClNO
2-aMino-3-(2-Methoxybenzoyl)-5-broMopyridine 2-aMino-3-(2-Methoxybenzoyl)-5-broMopyridine 875639-76-2 C13H11BrN2O2
(3R)-1-Methyl-3-PyrrolidinaMine hydrochloride (3R)-1-Methyl-3-PyrrolidinaMine hydrochloride 403712-80-1 C5H13ClN2
IMidazo[1,2-a]pyridine, 6-fluoro-2-phenyl- IMidazo[1,2-a]pyridine, 6-fluoro-2-phenyl- 1126635-20-8 C13H9FN2
(1H,1H,2H,2H-PERFLUORO-N-HEXYL)METHYLDICHLORO-SILANE (1H,1H,2H,2H-PERFLUORO-N-HEXYL)METHYLDICHLORO-SILANE 38436-16-7 C7H7Cl2F9Si
(2R,4S)-1-FMoc-4-BOC-aMino Pyrrolidine-2-carboxylic acid (2R,4S)-1-FMoc-4-BOC-aMino Pyrrolidine-2-carboxylic acid 1820570-42-0 C25H28N2O6
1-Ethyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide 1-Ethyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide 223436-99-5 C9H16F6N2O4S2
2-(3,4-diMethoxybenzyl)-7-((2S,3S)-2-hydroxy-6-phenylhexan-3-yl)-5-MethyliMidazo[1,5-f][1,2,4]triazin-4(3H)-one 2-(3,4-diMethoxybenzyl)-7-((2S,3S)-2-hydroxy-6-phenylhexan-3-yl)-5-MethyliMidazo[1,5-f][1,2,4]triazin-4(3H)-one 439083-91-7 C27H32N4O4
2-broMo-5-iodoiMidazo[2,1-b]thiazole 2-broMo-5-iodoiMidazo[2,1-b]thiazole 1379307-48-8 C5H2BrIN2S
3-BroMo-8-Methyl-iMidazo[1,2-a]pyridine-2-carboxylic acid 3-BroMo-8-Methyl-iMidazo[1,2-a]pyridine-2-carboxylic acid 1313712-29-6 C9H7BrN2O2
IMidazo[1,2-a]pyriMidine hydrochloride IMidazo[1,2-a]pyriMidine hydrochloride 6840-21-7 C6H6ClN3
1-propenyl-3-MethyliMidazoliuM perchlorate 1-propenyl-3-MethyliMidazoliuM perchlorate 1366043-39-1 C7H11ClN2O4
1H-lMidazoliuM,2-[[(4S,5S)-1,3-diMiethyl-4,5-diphenyl-2-iMidazolinydene]aMino]-4,5-dihydro-1,3-diMethyl-4,5-diphenyl-,choride(1:1),(4S,5S)- 1H-lMidazoliuM,2-[[(4S,5S)-1,3-diMiethyl-4,5-diphenyl-2-iMidazolinydene]aMino]-4,5-dihydro-1,3-diMethyl-4,5-diphenyl-,choride(1:1),(4S,5S)- 1268449-00-8 C34H36ClN5
2-(4-Bromophenyl)-4-phenylquinazoline 2-(4-Bromophenyl)-4-phenylquinazoline 540466-42-0 C20H13BrN2
(R)-N-(2-oxo-2-(pyrrolidin-3-ylaMino)-ethyl)-3-(trifluoroMethyl)benzaMide (R)-N-(2-oxo-2-(pyrrolidin-3-ylaMino)-ethyl)-3-(trifluoroMethyl)benzaMide 226249-16-7 C14H16F3N3O2
1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole 575452-22-1 C7H11IN2O
3-(4-BroMophenyl)pyrrolidine hydrochloride 3-(4-BroMophenyl)pyrrolidine hydrochloride 1187931-39-0 C10H13BrClN
MethaniMidaMide, N'-[1-cyclopropyl-3-(2-fluoro-4-iodophenyl)-1,2,3,6-tetrahydro-2,6-dioxo-4-pyriMidinyl]-N,N-diMethyl- MethaniMidaMide, N'-[1-cyclopropyl-3-(2-fluoro-4-iodophenyl)-1,2,3,6-tetrahydro-2,6-dioxo-4-pyriMidinyl]-N,N-diMethyl- 871700-30-0 C16H16FIN4O2
Furo[2,3-d]pyriMidine, 4-chloro-5,6-diphenyl- Furo[2,3-d]pyriMidine, 4-chloro-5,6-diphenyl- 65148-07-4 C18H11ClN2O
4-Cyano-2-Methylphenylboronic acid, pinacol ester 4-Cyano-2-Methylphenylboronic acid, pinacol ester 848953-05-9 C14H18BNO2
1,4-Di(1H-pyrazol-4-yl)benzene 1,4-Di(1H-pyrazol-4-yl)benzene 1036248-62-0 C12H10N4
(E)-1,1,1-Trichloro-4-ethoxy-but-3-en-2-one (E)-1,1,1-Trichloro-4-ethoxy-but-3-en-2-one 59938-07-7 C6H7Cl3O2
9-Boc-3-oxa-7,9-diazabicyclo[3.3.1]nonane 9-Boc-3-oxa-7,9-diazabicyclo[3.3.1]nonane 1251010-45-3 C11H20N2O3
5-(3-Hydroxypropyl)-2,4(1H,3H)-pyriMidinedione 5-(3-Hydroxypropyl)-2,4(1H,3H)-pyriMidinedione 53761-38-9 C7H10N2O3
3-(piperidin-4-yl)pyridine hydrochloride 3-(piperidin-4-yl)pyridine hydrochloride 690261-73-5 C10H15ClN2
4-BroMo-1H-iMidazole-2-carboxylic acid 4-BroMo-1H-iMidazole-2-carboxylic acid 1260753-02-3 C4H3BrN2O2
4-Methoxyindole 4-Methoxyindole 4837-90-5 C9H9NO
6-Chloro-1-Methyl-1H-iMidazo[4,5-c]pyridine 6-Chloro-1-Methyl-1H-iMidazo[4,5-c]pyridine 7205-46-1 C7H6ClN3
(2S)-N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-2-Pyrrolidinecarboxamide (2S)-N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-2-Pyrrolidinecarboxamide 529486-25-7 C19H22N2O2
ethyl 2-(3-((pyrrolidin-1-yl)methyl)benzylamino)acetate ethyl 2-(3-((pyrrolidin-1-yl)methyl)benzylamino)acetate 1228587-58-3 C16H24N2O2
(R)-2-Acetyl-pyrrolidine hydrochloride (R)-2-Acetyl-pyrrolidine hydrochloride 1373232-21-3 C6H12ClNO
7-HYDROXY-5-METHYL-2-METHYLTHIO-S-TRIAZOLO[1,5-A]PYRIMIDINE 7-HYDROXY-5-METHYL-2-METHYLTHIO-S-TRIAZOLO[1,5-A]PYRIMIDINE 40775-78-8 C7H8N4OS
5-PHENYL-1H-1,2,3-TRIAZOLE 5-PHENYL-1H-1,2,3-TRIAZOLE 1680-44-0 C8H7N3
3-Methylpiperidin-4-one hydrochloride 3-Methylpiperidin-4-one hydrochloride 4629-78-1 C6H12ClNO
7-Chloro-3-iodoimidazo(1,2-B)pyridazine 7-Chloro-3-iodoimidazo(1,2-B)pyridazine 1383481-13-7 C6H3ClIN3
3-Bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide 3-Bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide 1788044-16-5 C7H9Br2NS
5-bromo-N-butyl-7-((1r,4r)-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine 5-bromo-N-butyl-7-((1r,4r)-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine 1429882-29-0 C22H37BrN4OSi
1-Octyl-1H-benzo[d]imidazole 1-Octyl-1H-benzo[d]imidazole 42032-46-2 C15H22N2
5-FLUORO-2-METHYLBENZIMIDAZOLE 5-FLUORO-2-METHYLBENZIMIDAZOLE 118469-15-1 C8H7FN2
3-Methyl-6-(trifluoromethyl)imidazo[2,1-b]thiazole-5-carboxylic acid 3-Methyl-6-(trifluoromethyl)imidazo[2,1-b]thiazole-5-carboxylic acid 1368302-66-2 C8H5F3N2O2S
2-bromo-1H-imidazole-5-carboxylic acid 2-bromo-1H-imidazole-5-carboxylic acid 944901-01-3 C4H3BrN2O2
5-(bromomethyl)pyrazolo[1,5-a]pyrimidine 5-(bromomethyl)pyrazolo[1,5-a]pyrimidine 1228351-80-1 C7H6BrN3
2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Imidazo[1,2-a]pyridine 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Imidazo[1,2-a]pyridine 1352391-12-8 C14H19BN2O2
1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate 1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate 251924-83-1 C12H19NO5
3-bromoimidazo[5,1-b]thiazole 3-bromoimidazo[5,1-b]thiazole 1279721-68-4 C5H3BrN2S
1H-Benzimidazole, 1-(4-bromophenyl)-2-ethyl- 1H-Benzimidazole, 1-(4-bromophenyl)-2-ethyl- 97870-64-9 C15H13BrN2
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