Methanesulfonyl chloride → 4-(2-methanesulfonylamino-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

HRID 429641Notes

Reaction equation

HRID 429641 reaction equation
[NH2:1][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][S:49](Cl)(=[O:51])=[O:50]>N1C=CC=CC=1>[CH3:48][S:49]([NH:1][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)(=[O:51])=[O:50]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 183549364-(2-amino-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 183548044-(2-methanesulfonylamino-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideYield 14.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(2-amino-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (90 mg) in pyridine (1 ml) was added methanesulfonyl chloride (18 mg) in ice water bath under nitrogen and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in chloroform. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution, water and brine and the solution was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1) to give 4-(2-methanesulfonylamino-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (15 mg) as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate solution, water and brine
  4. dry with materialthe solution was dried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1)

Sources & evidence

ORD record
ord-d88a537f0a9449c69719b5f8cb03af6d
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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