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

HRID 2093372Notes

Reaction equation

HRID 2093372 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 II (1.0 g) was refluxed for 16 hours with 30 ml of water. 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 0.89 g 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-9de9bfdd954b4747aae22eca8f34972f
Source dataset
uspto-grants-2013_05
Patent number
US08445496B2

Reaction notes

Loading…