3-Ethoxycarbonyl-7-(3-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid → 3-Ethoxycarbonyl-6-(6-fluoro-2h-spiro[benzofuran-3,4'-piperidine]-1'-ylcarbonyl)-7-(3-methylphenylamino)pyrazolo[1,5-a]pyrimidine

HRID 1027091Notes

Reaction equation

HRID 1027091 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]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)=[C:13]([C:23]([OH:25])=O)[CH:12]=[N:11][C:10]=12)=[O:5])[CH3:2].Cl.[F:27][C:28]1[CH:33]=[CH:32][C:31]2[C:34]3([CH2:40][O:41][C:30]=2[CH:29]=1)[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3>>[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]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=3)=[C:13]([C:23]([N:37]3[CH2:38][CH2:39][C:34]4([C:31]5[CH:32]=[CH:33][C:28]([F:27])=[CH:29][C:30]=5[O:41][CH2:40]4)[CH2:35][CH2:36]3)=[O:25])[CH:12]=[N:11][C:10]=12)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 675408833-Ethoxycarbonyl-7-(3-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acidHCID 675414026-Fluoro-2H-spiro[1-benzofuran-3,4'-piperidine] hydrochloride

Product 1

HCID 675408513-Ethoxycarbonyl-6-(6-fluoro-2h-spiro[benzofuran-3,4'-piperidine]-1'-ylcarbonyl)-7-(3-methylphenylamino)pyrazolo[1,5-a]pyrimidineYield 64.3%

Procedure

In the same manner as in Example 21, step 5 and using 3-ethoxycarbonyl-7-(3-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.130 g, 0.382 mmol) obtained in step 2 and 6-fluoro-2H-spiro[benzofuran-3,4′-piperidine]hydrochloride (0.087 g, 0.420 mmol), the title compound (0.130 g, 64%) was obtained.

Sources & evidence

ORD record
ord-eccdf4cd5940418ca04dec47ef738642
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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