4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile → Bosutinib monohydrate

HRID 499135Notes

Reaction equation

HRID 499135 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][C:13]=1[C:35]#[N:36]>O>[OH2:9].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][C:13]=1[C:35]#[N:36]

Participants

3

Reactant 1

HCID 53289404-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile

Product 1

HCID 11990828Bosutinib monohydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile, Form III (2.0 g) was stirred for 24 hours with 40 ml of water at 95° C. The mixture was cooled to room temperature and filtered. The cake was washed with 10 ml of water and vacuum dried at 45° C. to give 1.83g of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile monohydrate, Form I by XRD scans.

Workup

  1. filtrationfiltered
  2. washThe cake was washed with 10 ml of water and vacuum
  3. customdried at 45° C.

Sources & evidence

ORD record
ord-0a542a3e32824052bce2c530c9a11c75
Source dataset
uspto-grants-2010_08
Patent number
US07767678B2

Reaction notes

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