m-Toluidine → 3-Ethoxycarbonyl-7-(3-methylphenylamino)-6-(2H-spiro[benzofuran-3,4'-piperidine]-1'-ylcarbonyl)pyrazolo[1,5-a]pyrimidine

HRID 1027084Notes

Reaction equation

HRID 1027084 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]2[N:5]=[CH:4][C:3]=1[C:16]([N:18]1[CH2:23][CH2:22][C:21]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[O:25][CH2:24]2)[CH2:20][CH2:19]1)=[O:17].[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=1>>[CH2:14]([O:13][C:11]([C:10]1[CH:9]=[N:8][N:7]2[C:2]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=3)=[C:3]([C:16]([N:18]3[CH2:23][CH2:22][C:21]4([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=5[O:25][CH2:24]4)[CH2:20][CH2:19]3)=[O:17])[CH:4]=[N:5][C:6]=12)=[O:12])[CH3:15]

Participants

3

Reactant 2

HCID 7934m-ToluidineHCID 866462987-Chloro-3-ethoxycarbonyl-6-(2H-spiro[benzofuran-3,4'-piperidine]-1'-ylcarbonyl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 675412973-Ethoxycarbonyl-7-(3-methylphenylamino)-6-(2H-spiro[benzofuran-3,4'-piperidine]-1'-ylcarbonyl)pyrazolo[1,5-a]pyrimidineYield 92%

Procedure

In the same manner as in Example 19, step 5 and using 7-chloro-3-ethoxycarbonyl-6-(2H-spiro[benzofuran-3,4′-piperidine]-1′-ylcarbonyl)pyrazolo[1,5-a]pyrimidine (0.2 g, 0.45 mmol) obtained in Example 128, step 2 and m-toluidine (0.073 g, 0.68 mmol), the title compound (0.21 g, 92%) was obtained.

Sources & evidence

ORD record
ord-f838e71b461547719e8501bd2fd5eda1
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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