2-(4-amino-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide → 2-(4-{[7-(benzyloxy)-6-fluoroquinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide hydrochloride

HRID 639988Notes

Reaction equation

HRID 639988 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][C:10]=1[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:23]=[N:24][N:25]([CH2:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)=[O:29])[CH:26]=1>C(O)(C)C.C(OCC)C>[ClH:19].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:21][C:22]3[CH:23]=[N:24][N:25]([CH2:27][C:28]([NH:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=4)=[O:29])[CH:26]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 283740072-(4-amino-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamideHCID 866052297-(Benzyloxy)-4-chloro-6-fluoroquinazoline

Product 1

HCID 686381152-(4-{[7-(benzyloxy)-6-fluoroquinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide hydrochlorideYield 95.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-(benzyloxy)-4chloro-6-fluoroquinazoline (0.288 g, 1.0 mmol) and 2-(4-amino-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide (0.234 g, 1.0 mmol) in isopropanol (5 ml) was heated at 80° C. for 10 minutes. The mixture was allowed to cool to room temperature and then diluted with diethyl ether. The resultant solid was filtered to give 2-(4-{[7-(benzyloxy)-6-fluoroquinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(3-fluorophenyl)acetamide hydrochloride (0.499 g, 95% yield) as a yellow solid:

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resultant solid was filtered

Sources & evidence

ORD record
ord-24c3c584a3ca494f8965b881e41c36de
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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