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

HRID 1027088Notes

Reaction equation

HRID 1027088 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([Br:18])=[C:13]2[N:12]=[CH:11][C:10]=1[C:19]([OH:21])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[F:23][C:24]1[CH:29]=[CH:28][C:27]2[C:30]3([CH2:36][O:37][C:26]=2[CH:25]=1)[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3>>[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([Br:18])=[C:13]2[N:12]=[CH:11][C:10]=1[C:19]([N:33]1[CH2:34][CH2:35][C:30]2([C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][C:26]=3[O:37][CH2:36]2)[CH2:31][CH2:32]1)=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 675403637-Benzylamino-3-bromopyrazolo[1,5-a]pyrimidine-6-carboxylic acidHCID 675414026-Fluoro-2H-spiro[1-benzofuran-3,4'-piperidine] hydrochloride

Product 1

HCID 675414047-Benzylamino-3-bromo-6-(6-fluoro-2h-spiro[benzofuran-3,4'-piperidine]-1'-ylcarbonyl)pyrazolo[1,5-a]pyrimidineYield 77.8%

Procedure

In the same manner as in Example 21, step 5 and using 7-benzylamino-3-bromopyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.193 g, 0.556 mmol) obtained in Example 22, step 3 and 6-fluoro-2H-spiro[benzofuran-3,4′-piperidine]hydrochloride (0.150 g, 0.616 mmol) obtained in Reference Example 4, the title compound (0.232 g, 77%) was obtained.

Workup

  1. customobtained in Reference Example 4

Sources & evidence

ORD record
ord-b5bae90810d140a3b0507672c18a9be8
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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