1-Methylpiperazine → 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-[2-(4-methylpiperazin-1-yl)-1H-benzimidazol-4-yl]carbonylaminobenzamide

HRID 429693Notes

Reaction equation

HRID 429693 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([NH:13][C:14]3[CH:45]=[CH:44][C:17]([C:18]([N:20]([CH3:43])[C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=4[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([N:36]4[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]4)=[O:35])=[O:19])=[CH:16][C:15]=3[O:46][CH3:47])=[O:12])[C:4]=2[N:3]=1.[CH3:48][N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>>[CH3:47][O:46][C:15]1[CH:16]=[C:17]([CH:44]=[CH:45][C:14]=1[NH:13][C:11]([C:10]1[C:4]2[N:3]=[C:2]([N:52]3[CH2:53][CH2:54][N:49]([CH3:48])[CH2:50][CH2:51]3)[NH:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)=[O:12])[C:18]([N:20]([CH3:43])[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]1)=[O:35])=[O:19]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 183547984-[2-chloro-1H-benzimidazol-4-yl]carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

Product 1

HCID 183547993-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-[2-(4-methylpiperazin-1-yl)-1H-benzimidazol-4-yl]carbonylaminobenzamideYield 86%

Procedure

A solution of 4-[2-chloro-1H-benzimidazol-4-yl]carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (70 mg) and N-methylpiperazine (106 mg) was heated at 80° C. for 2.5 hours. The excess of N-methylpiperazine was evaporated in vacuo and the residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1) to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-[2-(4-methylpiperazin-1-yl)-1H-benzimidazol-4-yl]carbonylaminobenzamide (66 mg).

Workup

  1. customThe excess of N-methylpiperazine was evaporated in vacuo
  2. customthe residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-a247def416dd45729d19336d3717a6da
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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