Pyridine → 4-(2-nitrobenzenesulfonyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

HRID 1005592Notes

Reaction equation

HRID 1005592 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([N:8]([CH3:31])[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[O:23])=[O:7])=[CH:4][C:3]=1[O:34][CH3:35].N1C=CC=CC=1.[N+:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[S:51](Cl)(=[O:53])=[O:52])([O-:44])=[O:43]>ClCCl>[N+:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[S:51]([NH:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([N:8]([CH3:31])[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[O:23])=[O:7])=[CH:4][C:3]=1[O:34][CH3:35])(=[O:53])=[O:52])([O-:44])=[O:43]

Participants

5

Reactant 3

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 183549064-amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

Product 1

HCID 187912334-(2-nitrobenzenesulfonyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (327 mg) and pyridine (80.3 mg) in dichloromethane (6 ml) was added dropwise 2-nitrobenzenesulfonyl chloride (150 mg) at ambient temperature and the mixture was stirred at ambient temperature for 5 hours. The resulting mixture was diluted with dichloromethane (10 ml) and the organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of solvents afforded a crude product. The crude product was chromatographed on silica gel (eluent; 2-4% methanol in chloroform) to give 4-(2-nitrobenzenesulfonyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (460 mg).

Workup

  1. washthe organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine
  2. customDrying
  3. filtrationfiltering
  4. customremoval of solvents
  5. customafforded a crude product
  6. customThe crude product was chromatographed on silica gel (eluent; 2-4% methanol in chloroform)

Sources & evidence

ORD record
ord-c4445933875c4d868e23a7715b3bb366
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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