3-Bromo-7-(4-fluoro-2-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid → 3-Bromo-6-[4-fluoro-4-(4-fluorophenyl)piperidine-1-carbonyl]-7-(4-fluoro-2-methylphenylamino)pyrazolo[1,5-a]pyrimidine

HRID 1027039Notes

Reaction equation

HRID 1027039 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[CH3:19])=[C:9]([C:20](O)=[O:21])[CH:8]=[N:7][C:6]=12.Cl.[F:24][C:25]1([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[CH3:19])=[C:9]([C:20]([N:28]3[CH2:27][CH2:26][C:25]([F:24])([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH2:30][CH2:29]3)=[O:21])[CH:8]=[N:7][C:6]=12

Participants

3

Reactant 2

HCID 675400523-Bromo-7-(4-fluoro-2-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acidHCID 675408264-Fluoro-4-(4-fluorophenyl)piperidine hydrochloride

Product 1

HCID 675406323-Bromo-6-[4-fluoro-4-(4-fluorophenyl)piperidine-1-carbonyl]-7-(4-fluoro-2-methylphenylamino)pyrazolo[1,5-a]pyrimidineYield 48.3%

Procedure

In the same manner as in Example 21, step 5 and using 3-bromo-7-(4-fluoro-2-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid (100 mg, 0.27 mmol) obtained in step 2 and 4-fluoro-4-(4-fluorophenyl)piperidine hydrochloride (WO2008/012622, 71 mg, 0.33 mmol), the title compound (71 mg, 48%) was obtained.

Sources & evidence

ORD record
ord-490e8e22aa7a4e628207b799a85b0c41
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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