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

HRID 1027100Notes

Reaction equation

HRID 1027100 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][C:19]([CH3:22])=[C:18]([F:23])[CH:17]=3)=[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:34]=[CH:33][C:32]2[C:35]3([CH2:41][O:42][C:31]=2[CH:30]=1)[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]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][C:19]([CH3:22])=[C:18]([F:23])[CH:17]=3)=[C:13]([C:24]([N:38]3[CH2:37][CH2:36][C:35]4([C:32]5[CH:33]=[CH:34][C:29]([F:28])=[CH:30][C:31]=5[O:42][CH2:41]4)[CH2:40][CH2:39]3)=[O:25])[CH:12]=[N:11][C:10]=12)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 675403653-Ethoxycarbonyl-7-(3-fluoro-4-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acidHCID 675414026-Fluoro-2H-spiro[1-benzofuran-3,4'-piperidine] hydrochloride

Product 1

HCID 675405493-Ethoxycarbonyl-7-(3-fluoro-4-methylphenylamino)-6-(6-fluoro-2h-spiro[benzofuran-3,4'-piperidine]-1'-ylcarbonyl)pyrazolo[1,5-a]pyrimidineYield 96.1%

Procedure

In the same manner as in Example 21, step 5 and using 3-ethoxycarbonyl-7-(3-fluoro-4-methylphenylamino)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.130 g, 0.363 mmol) obtained in step 2 and 6-fluoro-2H-spiro[benzofuran-3,4′-piperidine]hydrochloride (0.082 g, 0.399 mmol), the title compound (0.191 g, 96%) was obtained.

Sources & evidence

ORD record
ord-2f717f0f6c1a47d6a12f105bf2fa8223
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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