1-Methylpiperazine → Rac-6-chloro-3-(3-chloro-benzyl)-3-[3-(4-methyl-piperazine-1-carbonyl)-phenylamino]-1,3-dihydro-indol-2-one

Reaction equation

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

Participants

Reactant 3

HCID 531671-Methylpiperazine

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

HCID 57507310Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-ylamino]-benzoic acid

Product 1

HCID 24950103Rac-6-chloro-3-(3-chloro-benzyl)-3-[3-(4-methyl-piperazine-1-carbonyl)-phenylamino]-1,3-dihydro-indol-2-one

Procedure

The mixture of rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoic acid (60 mg, 0.14 mmol), 1-methyl-piperazine (56 mg, 0.56 mmol) and EDCl (54 mg, 0.28 mmol) in dichlorometahne (2 mL) was stirred at room temperature for overnight. The reaction mixture was purified by preparative HPLC to give rac-6-chloro-3-(3-chloro-benzyl)-3-[3-(4-methyl-piperazine-1-carbonyl)-phenylamino]-1,3-dihydro-indol-2-one as a powder. 1H NMR (CDCl3, 400 MHz): δ 7.21-6.74 (m, 9H), 6.49 (d, 1H), 6.17 (s, 1H), 4.70 (s, 1H), 3.80-3.45 (br, 8H), 3.28-3.15 (q, 2H), 2.66 (s, 3H). MS: [M+H]+=509