7-(Benzyloxy)-4-chloroquinazoline → 2-(4-{[7-(benzyloxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide hydrochloride

HRID 640005Notes

Reaction equation

HRID 640005 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:19])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][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])[CH:31]=2)=[O:28])[CH:25]=1>CC(N(C)C)=O.C(OCC)C>[ClH:19].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([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])[CH:31]=4)=[O:28])[CH:25]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 220309237-(Benzyloxy)-4-chloroquinazolineHCID 283740072-(4-amino-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide

Product 1

HCID 686390952-(4-{[7-(benzyloxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide hydrochlorideYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-(benzyloxy)-4-chloroquinazoline (1.94 g, 7.17 mmol) and 2-(4-amino-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide (1.66 g, 7.09 mmol) in dimethylacetamide (25 ml) was heated at 90° C. for 1 hour. The mixture was cooled to room temperature and then diluted with diethyl ether (75 ml) and filtered. The solid was washed with diethyl ether and dried to yield 2-(4-{[7-(benzyloxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide hydrochloride (2.92 g, 82% yield) as a yellow solid:

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-a03ec6f5ef9649998411dd565e408ab9
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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