| Identification | Back Directory | [Name]
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester | [CAS]
74936-72-4 | [Synonyms]
PRAN-001
278-034-2
Le Chi Chi
1,4-DHPCOOH
Nicardipine USP RC A
Nifedipine Impurity 2
Le Chi mother nucleus
Lercanidipine nucleus
Benidipine Impurity 18
Nimodipine Impurity 7
Lercanidipine mainring
Benidipine Intermediate
Lercanidipine Impurity 9
-2,6-dimethyl-4-(3-nitrophenyl)
Le Cardipine Main Ring Reference
Nicardipine USP Related Compound A
1,4-Dihydro-2,6-dimethyl-4-(3-nitro
-1,4-dihydropyridine-3-carboxylic acid
Nicardipine Carboxylic Acid Derivative
2,6-DI-ME-4-(3-NITRO-PH)-1,4-2H-PYRIDINE-3,5-DICAR
1,4-Dihydro-2,6-diMethyl-4-(3-nitrophenyl)-3,5-pyr
Nicardipine Carboxylic Acid Derivative (Nifedipine Impurity 2)
Nifedipine Impurity 2 (Nicardipine Carboxylic Acid Derivative )
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
Nicardipine Related Compound A (Nicardipine Carboxylic Acid Impurity)
2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester
Monomethyl 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
Monomethyl 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate >
1,4-DIHYDRO-5-METHOXYCARBONYL-2,6-DIMETHYL-4-(3-NITROPHENYL)PYRIDINE-3-CARBOXYLIC AC
Methyl hydrogen 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
2,6-DiMethyl-5-Methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydorpyridine-3-carboxylic acid
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-methyl ester
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester
2,6-DIMETHYL-5-METHOXY CARBONYL-4-(3-NITRO-PHENYL)-1,4-DIHYDROPYRIDINE-3-CARBOXYLIC ACID
2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydroxypyridine-3-carboxylic acid
3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-diMethyl-4-(3-nitrophenyl)-, 3-Methyl ester
rac-1,4-Dihydro-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic Acid
2,6-dimethyl-5-methoxycarbonyl-4-(3-nitro phenyl)-1,4 dihydropyridine-3-carboxylic acid (74936-72-4)
PHARMACEUTICAL RAW MATERIAL : 2,6-DIMETHYL-5-METHOXYCARBONYL-4-(3-NITROPHENYL)-1,4- DIHYDROPYRIDINE -3- CARBOXYLIC ACID | [EINECS(EC#)]
278-034-2 | [Molecular Formula]
C16H16N2O6 | [MDL Number]
MFCD00475478 | [MOL File]
74936-72-4.mol | [Molecular Weight]
332.31 |
| Chemical Properties | Back Directory | [Melting point ]
200-202?C | [Boiling point ]
505.0±50.0 °C(Predicted) | [density ]
1.345±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
DMSO (Sparingly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
1.66±0.70(Predicted) | [color ]
Pale Yellow to Light Yellow | [InChI]
InChI=1S/C16H16N2O6/c1-8-12(15(19)20)14(13(9(2)17-8)16(21)24-3)10-5-4-6-11(7-10)18(22)23/h4-7,14,17H,1-3H3,(H,19,20) | [InChIKey]
JPXPPUOCSLMCHK-UHFFFAOYSA-N | [SMILES]
C1(C)NC(C)=C(C(O)=O)C(C2=CC=CC([N+]([O-])=O)=C2)C=1C(OC)=O |
| Hazard Information | Back Directory | [Description]
5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid(1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester) is a pharmaceutical intermediate ingredient used in the preparation of Barnidipine, Lercanidipine hydrochloride and nitrendipine analogues. These drugs are all calcium channel blockers and are used to treat various forms of hypertension. | [Chemical Properties]
Light-Yellow Solid | [Uses]
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester can be used in the prevention and therapy of atherosclerotic degradation of arterial walls.
| [Synthesis]
General procedure for the synthesis of monomethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate from dimethyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate:
(3) Preparation of 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
Dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (0.01 mol) was mixed with 150 mL of methanol. Saturated aqueous NaOH solution (9 g, 0.225 mol) was slowly added to the mixture under stirring conditions. The reaction mixture was vigorously stirred at 70 °C for 6 hours. Upon completion of the reaction, about 80 mL of methanol was removed by evaporation under reduced pressure. 200 mL of water was added to the residue and unreacted feedstock was removed by filtration. The filtrate was adjusted to pH about 2.5 with 1 mol/L hydrochloric acid, at which point a yellow solid precipitated, which was filtered and dried to give a khaki colored powder. The resulting powder was recrystallized from methanol to give the title product 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid monomethyl ester as a yellow solid (1.9 g, 57.2% yield). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 805 - 808
[2] Patent: US2014/45896, 2014, A1. Location in patent: Paragraph 0071; 0072
[3] Patent: EP2703398, 2014, A1. Location in patent: Paragraph 0067; 0068
[4] Patent: CN106279000, 2017, A. Location in patent: Paragraph 0032; 0033; 0034; 0035; 0036; 0037; 0038
[5] European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 3986 - 3992 |
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