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

HRID 1027041Notes

Reaction equation

HRID 1027041 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]2[N:13]=[CH:12][C:11]=1[C:24]([OH:26])=O.Cl.[F:28][C:29]1([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]2[N:13]=[CH:12][C:11]=1[C:24]([N:32]1[CH2:31][CH2:30][C:29]([F:28])([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[CH2:34][CH2:33]1)=[O:26]

Participants

3

Reactant 2

HCID 675407397-(2,5-Dimethylphenylamino)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acidHCID 675408264-Fluoro-4-(4-fluorophenyl)piperidine hydrochloride

Product 1

HCID 675406927-(2,5-Dimethylphenylamino)-3-ethoxycarbonyl-6-[4-fluoro-4-(4-fluorophenyl)piperidine-1-carbonyl]pyrazolo[1,5-a]pyrimidineYield 54%

Procedure

In the same manner as in Example 21, step 5 and using 7-(2,5-dimethylphenylamino)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (100 mg, 0.28 mmol) obtained in Example 88, step 2 and 4-fluoro-4-(4-fluorophenyl)piperidine hydrochloride (79 mg, 0.34 mmol), the title compound (80 mg, 54%) was obtained.

Sources & evidence

ORD record
ord-f111c9bbd9794fbea84e36531a82143c
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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