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

HRID 1533769Notes

Reaction equation

HRID 1533769 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]([NH:12][C:13]3[CH:44]=[CH:43][C:16]([C:17]([N:19]([CH3:42])[C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=4[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([N:35]4[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]4)=[O:34])=[O:18])=[CH:15][C:14]=3[O:45][CH3:46])=[O:11])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl-].C[CH:49]=[N+:50]=[CH:51]C.Cl[CH2:54]Cl>O>[CH3:49][N:50]([CH2:51][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[C:10]([NH:12][C:13]2[CH:44]=[CH:43][C:16]([C:17]([N:19]([CH3:42])[C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=3[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([N:35]3[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]3)=[O:34])=[O:18])=[CH:15][C:14]=2[O:45][CH3:46])=[O:11])[NH:1][CH:2]=1)[CH3:54]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 183548224-[(indol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideHCID 21873455N,N-dimethylmethylene ammonium chloride

Product 1

HCID 183551654-[(3-dimethylaminomethylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[(indol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (93 mg) in dichloromethane (6.0 ml) was added N,N-dimethylmethylene- ammonium chloride (41.7 mg) at 0° C. and the mixture was stirred at ambient temperature for 1 hour. The resulting mixture was diluted with water and the aqueous solution was extracted with dichloromethane. Drying, filtering and removal of solvents afforded 4-[(3-dimethylaminomethylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (90 mg) as a colorless syrup.

Workup

  1. extractionthe aqueous solution was extracted with dichloromethane
  2. customDrying
  3. filtrationfiltering
  4. customremoval of solvents

Sources & evidence

ORD record
ord-a407cbbd288647638e8e7db52125c783
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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