4-(3,4-Difluorophenyl)piperidine hydrochloride → 6-[4-(3,4-Difluorophenyl)piperidine-1-carbonyl]-3-ethoxycarbonyl-7-(2-fluoro-5-methylphenylamino)pyrazolo[1,5-a]pyrimidine

HRID 1027014Notes

Reaction equation

HRID 1027014 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([NH:15][C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=3[F:23])=[C:13]([C:24](O)=[O:25])[CH:12]=[N:11][C:10]=12)=[O:5])[CH3:2].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:13]3[CH:12]=[N:11][C:10]4[N:9]([N:8]=[CH:7][C:6]=4[C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:14]=3[NH:15][C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=3[F:23])=[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 675407743-Ethoxycarbonyl-7-(2-fluoro-5-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid

Product 1

HCID 675411746-[4-(3,4-Difluorophenyl)piperidine-1-carbonyl]-3-ethoxycarbonyl-7-(2-fluoro-5-methylphenylamino)pyrazolo[1,5-a]pyrimidineYield 28%

Procedure

In the same manner as in Example 21, step 5 and using 3-ethoxycarbonyl-7-(2-fluoro-5-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid (150 mg, 0.42 mmol) obtained in step 2 and 4-(3,4-difluorophenyl)piperidine hydrochloride (WO2004/069798, 127 mg, 0.55 mmol), the title compound (63 mg, 28%) was obtained.

Sources & evidence

ORD record
ord-7d64eb0cf858451da8b7e85086ea1377
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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