Dimethylamine, hydrochloride → HCID 18354909, compound

HRID 429638Notes

Reaction equation

HRID 429638 reaction equation
C(C1[NH:5][C:6]2[C:11](C=1)=[C:10]([C:13]([NH:15][C:16]1[CH:47]=[CH:46][C:19]([C:20]([N:22]([CH3:45])[C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=3[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([N:38]3[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]3)=[O:37])=[O:21])=[CH:18][C:17]=1[O:48][CH3:49])=[O:14])[CH:9]=[CH:8][CH:7]=2)(O)=O.Cl.CNC.[OH:54]N1C2C=CC=CC=2N=N1.Cl.[CH3:65][N:66]([CH3:75])[CH2:67][CH2:68][CH2:69]N=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH3:75][N:66]([CH3:65])[C:67]([C:68]1[NH:5][C:6]2[C:11]([CH:69]=1)=[C:10]([C:13]([NH:15][C:16]1[CH:47]=[CH:46][C:19]([C:20]([N:22]([CH3:45])[C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=3[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([N:38]3[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH2:43]3)=[O:37])=[O:21])=[CH:18][C:17]=1[O:48][CH3:49])=[O:14])[CH:9]=[CH:8][CH:7]=2)=[O:54]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18355134HCID 18355134, compound

Product 1

HCID 18354909HCID 18354909, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-[(2-carboxyindol-4-yl)-carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (60 mg), N,N-dimethylamine hydrochloride (7.7 mg) and 1-hydroxybenzotriazole (14.5 mg) in N,N-dimethylformamide (3.0 ml) was added a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (20.6 mg) in N,N-dimethylformamide (1.0 ml) and the mixture was stirred at ambient temperature for 4 hours. The resulting mixture was diluted with ethyl acetate and the organic layer was washed successively with saturated aqueous sodium bicarbonate solution and brine. Drying, filtering and removal of solvents afforded 4-[(2-dimethylaminocarbonylindol-4-yl)-carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (60 mg) as a yellow amorphous powder.

Workup

  1. washthe organic layer was washed successively with saturated aqueous sodium bicarbonate solution and brine
  2. customDrying
  3. filtrationfiltering
  4. customremoval of solvents

Sources & evidence

ORD record
ord-68a6056a85624cb88e21a855f5a9c5d6
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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