Trifluoroacetic acid → HCID 136355269, compound

HRID 639987Notes

Reaction equation

Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:22]=[N:23][N:24]([CH2:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=4[F:37])=[O:28])[CH:25]=3)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[F:38])C1C=CC=CC=1.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>>[F:38][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:10]=1[OH:9])[N:17]=[CH:16][N:15]=[C:14]2[NH:20][C:21]1[CH:22]=[N:23][N:24]([CH2:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=2[F:37])=[O:28])[CH:25]=1.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[F:38][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:10]=1[OH:9])[N:17]=[CH:16][N:15]=[C:14]2[NH:20][C:21]1[CH:22]=[N:23][N:24]([CH2:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=2[F:37])=[O:28])[CH:25]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68639019HCID 68639019, compound

Product 2

HCID 136355268HCID 136355268, compound

HCID 136355269HCID 136355269, compoundYield 100%

Procedure

A solution of 2-(4-{[7-(benzyloxy)-6-fluoroquinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(2,3-difluorophenyl)acetamide hydrochloride (1.90 g, 3.51 mmol) in trifluoroacetic acid (20 ml) was heated at 70° C. for 4 hours. The mixture was evaporated and the residue triturated with diethyl ether to give 2-{4-[(6-fluoro-7-hydroxyquinazolin-4-yl)amino]-1H-pyrazol-1-yl}-N-(2,3-difluorophenyl)acetamide as the trifluoroacetic acid salt (1.89 g, 100% yield) as a pale yellow solid:

Workup

customThe mixture was evaporated
customthe residue triturated with diethyl ether

Sources & evidence

ORD record: ord-7609b0d3f3b54a56a40d731e3f14c97e
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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