4-(3,4-Difluorophenyl)piperidine hydrochloride → 6-[4-(3,4-Difluorophenyl)piperidine-1-carbonyl]-7-(2,5-dimethylphenylamino)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine

HRID 1027010Notes

Reaction equation

HRID 1027010 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](O)=[O:25].Cl.[F:28][C:29]1[CH:30]=[C:31]([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH:32]=[CH:33][C:34]=1[F:35]>>[F:28][C:29]1[CH:30]=[C:31]([CH:36]2[CH2:41][CH2:40][N:39]([C:24]([C:11]3[CH:12]=[N:13][C:14]4[N:15]([N:16]=[CH:17][C:18]=4[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:10]=3[NH:9][C:3]3[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=3[CH3:1])=[O:25])[CH2:38][CH2:37]2)[CH:32]=[CH:33][C:34]=1[F:35]

Participants

3

Reactant 2

HCID 467355494-(3,4-Difluorophenyl)piperidine hydrochlorideHCID 675407397-(2,5-Dimethylphenylamino)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid

Product 1

HCID 675403836-[4-(3,4-Difluorophenyl)piperidine-1-carbonyl]-7-(2,5-dimethylphenylamino)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidineYield 70.1%

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 (220 mg, 0.62 mmol) obtained in step 2 and 4-(3,4-difluorophenyl)piperidine hydrochloride (WO2004/069798, 217 mg, 0.93 mmol), the title compound (232 mg, 70%) was obtained.

Sources & evidence

ORD record
ord-d7aec61cae654bf1baa604d265c3ba54
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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