4-Chloro-6-methoxyquinazolin-7-yl acetate → N-(3-fluorophenyl)-2-{4-[(7-hydroxy-6-methoxyquinazolin-4-yl)amino]-1H-pyrazol-1-yl}acetamide

HRID 639989Notes

Reaction equation

HRID 639989 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[O:9])[CH:6]=1.[C:18]([O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26](Cl)=[N:27][CH:28]=[N:29]2)=[CH:24][C:23]=1[O:33][CH3:34])(=[O:20])[CH3:19]>CC(N(C)C)=O.C(OCC)C>[C:18]([O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26]([NH:1][C:2]3[CH:3]=[N:4][N:5]([CH2:7][C:8]([NH:10][C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=4)=[O:9])[CH:6]=3)=[N:27][CH:28]=[N:29]2)=[CH:24][C:23]=1[O:33][CH3:34])(=[O:20])[CH3:19].[F:17][C:13]1[CH:12]=[C:11]([NH:10][C:8](=[O:9])[CH2:7][N:5]2[CH:6]=[C:2]([NH:1][C:26]3[C:25]4[C:30](=[CH:31][C:22]([OH:21])=[C:23]([O:33][CH3:34])[CH:24]=4)[N:29]=[CH:28][N:27]=3)[CH:3]=[N:4]2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 222438854-Chloro-6-methoxyquinazolin-7-yl acetateHCID 283740072-(4-amino-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide

Product 2

HCID 686397574-[(1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-4-yl)amino]-6-methoxyquinazolin-7-yl acetateHCID 136368566N-(3-fluorophenyl)-2-{4-[(7-hydroxy-6-methoxyquinazolin-4-yl)amino]-1H-pyrazol-1-yl}acetamideYield 175.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-(4-amino-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide (0.246 g, 1.05 mmol) and 4-chloro-6-methoxyquinazolin-7-yl acetate (see WO96/15118, 0.252 g, 1.0 mmol) in dimethylacetamide (5 ml) was heated at 90° C. for 2 hours. The mixture was allowed to cool to room temperature and then diluted with diethyl ether and filtered. The solid was washed with diethyl ether and then dried in vacuo to leave 4-[(1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-4-yl)amino]-6-methoxyquinazolin-7-yl acetate as a mixture with 15% N-(3-fluorophenyl)-2-{4-[(7-hydroxy-6-methoxyquinazolin-4-yl)amino]-1H-pyrazol-1-yl}acetamide (0.358 g, 78% yield):

Workup

  1. filtrationfiltered
  2. washThe solid was washed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-10813f885bee4ea9bb6c4d07e7900a99
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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