| Identification | Back Directory | [Name]
7-(3-CHLORO-PROPOXY)-4-(2,4-DICHLORO-5-METHOXY-PHENYLAMINO)-6-METHOXY-QUINOLINE-3-CARBONITRILE | [CAS]
380844-49-5 | [Synonyms]
Bosutinib Impurity 24
Bosutinib Impurity 31
Bosutinib intermediate
1-Chloro-1-desmethylpiperazinyl-bosutinib
7-(3-chloropropoxy)-4-(2,4-dichloro-5-methoxyanilino)-6-methoxyquinoline-3-carbonitrile
7-(3-Chloropropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile
7-(3-CHLORO-PROPOXY)-4-(2,4-DICHLORO-5-METHOXY-PHENYLAMINO)-6-METHOXY-QUINOLINE-3-CARBONITRILE
3-Quinolinecarbonitrile, 7-(3-chloropropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-
7-(3-CHLORO-PROPOXY)-4-(2,4-DICHLORO-5-METHOXY-PHENYLAMINO)-6-METHOXY-QUINOLINE-3-CARBONITRILE ISO 9001：2015 REACH | [Molecular Formula]
C21H18Cl3N3O3 | [MDL Number]
MFCD09833975 | [MOL File]
380844-49-5.mol | [Molecular Weight]
466.74 |
| Chemical Properties | Back Directory | [Melting point ]
183-186℃ | [Boiling point ]
585.6±50.0 °C(Predicted) | [density ]
1.43 | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly, Sonicated), DMSO (Slightly) | [form ]
Solid | [pka]
3.71±0.50(Predicted) | [color ]
Pale Yellow to Light Yellow | [InChI]
InChI=1S/C21H18Cl3N3O3/c1-28-18-9-17(14(23)7-15(18)24)27-21-12(10-25)11-26-16-8-20(30-5-3-4-22)19(29-2)6-13(16)21/h6-9,11H,3-5H2,1-2H3,(H,26,27) | [InChIKey]
GASHKCRNJZBFBE-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC(OC)=C(OCCCCl)C=2)C(NC2=CC(OC)=C(Cl)C=C2Cl)=C(C#N)C=1 |
| Hazard Information | Back Directory | [Uses]
1-Chloro-1-desmethylpiperazinyl-bosutinib is a useful intermediate in the green preparation of the anti-tumor agent Bosutinib (B676095). It is a COVID19-related research product. | [Synthesis]
4-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile (31.2 g, 0.10 mol), 2,4-dichloro-5-methoxyaniline (21.1 g, 0.11 mol), and pyridine hydrochloride (12.8 g, 0.11 mol) were used as raw materials and mixed in 2-methoxyethanol (150 g). The reaction mixture was heated to 120 °C and maintained at this temperature for 3 hours. After completion of the reaction, the suspension was cooled to room temperature. The reaction mixture was slowly poured into water (600 g) under continuous stirring. The resulting solid product was collected by filtration and washed with water (2 x 40 g). Subsequently, the product was dried at 50 °C to afford 7-(3-chloropropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-cyanoquinoline (35.9 g, 77% yield) as an off-white solid. The structure of the product was confirmed by 1H NMR, 13C NMR and mass spectrometry (ESI).1H NMR (400 MHz, DMSO-d6) δ: 2.28 (m, J = 6.0 Hz, 2H), 3.82 (t, J = 6.0 Hz, 2H), 3.87 (s, 3H), 3.97 (s, 3H), 4.30 (t, J = 6.0 Hz, 2H). 7.35 (s, 1H), 7.37 (s, 1H), 7.75 (s, 1H), 7.85 (s, 1H), 8.43 (s, 1H), 9.63 (s, 1H).13C NMR (100 MHz, DMSO-d6) δ: 31.9, 42.1, 56.7, 57.3, 65.8, 86.9, 102.4, 110.0, 113.1, 114.0, 117.4, 120.9, 123.6, 130.3, 136.7, 146.2, 149.8, 149.9, 151.3, 152.9, 154.5. mass spectrum (ESI) m/z: 468.0 [M + H]+. | [References]
[1] Heterocycles, 2014, vol. 89, # 12, p. 2806 - 2813
[2] Synthesis (Germany), 2015, vol. 47, # 20, p. 3133 - 3138
[3] Patent: CN103848785, 2016, B. Location in patent: Paragraph 0087; 0088
[4] Molecules, 2010, vol. 15, # 6, p. 4261 - 4266
[5] Journal of Medicinal Chemistry, 2001, vol. 44, # 23, p. 3965 - 3977 |
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