m-Chloroperbenzoic acid → HCID 57531662, compound

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[C:15]2[CH2:16][CH2:17][C:18]3[CH:19]=[N:20][C:21]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([N:31]5[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]5)=[CH:27][CH:26]=4)=[N:22][C:23]=3[C:14]=2[N:13]([CH3:38])[N:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C(OO)=[O:47])C=CC=1.C([O-])(O)=O.[Na+]>>[CH2:1]([NH:8][C:9]([C:11]1[C:15]2[CH2:16][CH2:17][C:18]3[CH:19]=[N:20][C:21]([NH:24][C:25]4[CH:26]=[CH:27][C:28]([N:31]5[CH2:32][CH2:33][N+:34]([CH3:37])([O-:47])[CH2:35][CH2:36]5)=[CH:29][CH:30]=4)=[N:22][C:23]=3[C:14]=2[N:13]([CH3:38])[N:12]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 70297m-Chloroperbenzoic acid

HCID 516892Sodium Bicarbonate

HCID 57444152N-benzyl-1-methyl-8-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Product 1

HCID 57531662HCID 57531662, compoundYield 66%

Procedure

To a solution of 39.4 mg (0.0774 mmol) of N-benzyl-1-methyl-8-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide, 17.4 mg (0.0774 mg) of 3-chlorobenzenecarboperoxoic acid were added and the mixture was stirred at room temperature. After 45 minutes an aqueous solution of NaHCO3 was added and the solvent removed. Treatment with methanol and filtration afforded 26.6 mg of the title compound (66% yield).