Dimethylformamide → HCID 19696447, compound

HRID 863678Notes

Reaction equation

HRID 863678 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:36][CH2:35][N:10]2[C:11]3[C:16]([C:17]([C:18]4[C:19](=[O:34])O[C:21](=[O:33])[C:22]=4[C:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]([CH3:32])[CH:24]=4)=[C:9]2[CH2:8]1)=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:3])[CH3:2].C[N:38](C)C=O>N>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:36][CH2:35][N:10]2[C:11]3[C:16]([C:17]([C:18]4[C:19](=[O:34])[NH:38][C:21](=[O:33])[C:22]=4[C:23]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]([CH3:32])[CH:24]=4)=[C:9]2[CH2:8]1)=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 10412974HCID 10412974, compound

Product 1

HCID 19696447HCID 19696447, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 115 mg of 3-[8-(2-acetoxyethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione in 1 ml of dimethylformamide and 2 ml of 33% aqueous ammonia was heated to 140° C. for 4 hours. The cooled mixture was evaporated and the residue was purified by chromatography on silica gel with ethyl acetate/petroleum ether (2:1). Crystallization from ethyl acetate/petroleum ether gave 13 mg of 3-[8-(2-acetoxyethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 272°-274° C.

Workup

  1. customThe cooled mixture was evaporated
  2. customthe residue was purified by chromatography on silica gel with ethyl acetate/petroleum ether (2:1)
  3. customCrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-b1bc4fe469bc4076a97e9be7b67100bb
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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