Hydrochloric Acid → 2-(4-{[7-(benzyloxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(2,3-difluorophenyl)acetamide

HRID 639965Notes

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])[C:12]=2[F:18])=[O:9])[CH:6]=1.[CH2:19]([O:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31](Cl)=[N:32][CH:33]=[N:34]2)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.O1CCOCC1>CC(N(C)C)=O.ClCCl>[CH2:19]([O:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31]([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])[C:12]=4[F:18])=[O:9])[CH:6]=3)=[N:32][CH:33]=[N:34]2)=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2-(4-amino-1H-pyrazol-1-yl)-N-(2,3-difluorophenyl)acetamide (504 mg, 2 mmol) was added to a solution of 7-(benzyloxy)-4-chloroquinazoline (541 mg, 2 mmol) in dimethylacetamide (10 ml) under argon. A solution of 4.0 N hydrochloric acid in dioxane (500 μl, 2 mmol) was added and the mixture was heated at 90° C. for 1.5 hours. The mixture was cooled, diluted with dichloromethane and the resultant precipitate recovered by filtration. The solid was washed with dichloromethane and diethyl ether and dried in vacuo to yield 2-(4-{[7-(benzyloxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(2,3-difluorophenyl)acetamide (850 mg, 81% yield):

Workup

temperatureThe mixture was cooled
filtrationthe resultant precipitate recovered by filtration
washThe solid was washed with dichloromethane and diethyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-a0029a5b8c9442e38f64adddc2528f2e
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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