Acumapimod → 3-(5-Amino-4-cyclopentanecarbonyl-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide

HRID 884808Notes

Reaction equation

HRID 884808 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=C(C#N)[CH:22]=1.C1([Mg]Br)CCCC1>>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:22]1)=[O:29]

Participants

3

Reactant 2

HCID 11338127AcumapimodHCID 178419650HCID 178419650, compound

Product 1

HCID 117725573-(5-Amino-4-cyclopentanecarbonyl-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide

Procedure

Similar procedure as in Example 17B except 3-[5-amino-4-(3-cyano-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide was used in place of 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide and cyclopentylmagnesium bromide was used in place of phenyl magnesium bromide. HPLC (4 minute 10-90 gradient) tR 2.54 min; MS m/z 353.19 [M+H]+.

Workup

  1. customHPLC (4 minute 10-90 gradient) tR 2.54 min

Sources & evidence

ORD record
ord-9733f5a9fc804dd689d3540460cdf581
Source dataset
uspto-grants-2012_08
Patent number
US08242117B2

Reaction notes

Loading…