Water → 3-[8-(formamidomethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

HRID 863672Notes

Reaction equation

HRID 863672 reaction equation
CS(O[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:20][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)=O.O.C[N:39](C)[CH:40]=[O:41]>N>[CH:40]([NH:39][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:20][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:41]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 196963343-[6,7,8,9-tetrahydro-8-(methylsulphonyloxymethyl)pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

Product 1

HCID 196963453-[8-(formamidomethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 120 mg of the pyrroledione product of Example 6 in 6 ml of dimethylformamide and 6 ml of 33% aqueous ammonia was heated to 140° C. for 6 hours. The cooled mixture was poured into water and the precipitate was filtered off. The product was purified by chromatography on silica gel with dichloromethane/acetic acid/methanol/water (60:18:2:3). Trituration with ethyl acetate gave 50 mg of 3-[8-(formamidomethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 332°-334° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. customThe product was purified by chromatography on silica gel with dichloromethane/acetic acid/methanol/water (60:18:2:3)

Sources & evidence

ORD record
ord-2aaee817950c456c92782894f4a65973
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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