1,1'-Thiocarbonyldiimidazole → 3-[6,7,8,9-tetrahydro-8-isothiocyanato-pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

HRID 863685Notes

Reaction equation

HRID 863685 reaction equation
Cl.NC[CH:4]1[CH2:33][CH2:32][N:7]2[C:8]3[C:13]([C:14]([C:15]4[C:16](=[O:31])[NH:17][C:18](=[O:30])[C:19]=4[C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]([CH3:29])[CH:21]=4)=[C:6]2[CH2:5]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C1N=C[N:36]([C:39](N2C=NC=C2)=[S:40])C=1>CN(C)C=O.O1CCCC1>[N:36]([CH:4]1[CH2:33][CH2:32][N:7]2[C:8]3[C:13]([C:14]([C:15]4[C:16](=[O:31])[NH:17][C:18](=[O:30])[C:19]=4[C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]([CH3:29])[CH:21]=4)=[C:6]2[CH2:5]1)=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:39]=[S:40]

Participants

5

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 11539879Bisindolylmaleimide X hydrochloride

Product 1

HCID 196963273-[6,7,8,9-tetrahydro-8-isothiocyanato-pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dioneYield 59.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 505 mg of the pyrroledione product of Example 2 in 20 ml of dimethylformamide was treated with a solution of 222 mg of 1,1-thiocarbonyldiimidazole in 5 ml of tetrahydrofuran. After 17 hours the solvent was evaporated and the residue was purified by chromatography on silica gel with methanol/dichloromethane (1:99). Trituration with n-hexane gave 297 mg of 3-[6,7,8,9-tetrahydro-8-isothiocyanato-pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione in the form of a red solid of melting point 285°-287° C.

Workup

  1. customAfter 17 hours the solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel with methanol/dichloromethane (1:99)

Sources & evidence

ORD record
ord-216cbb93453a4997a9e81755faf7486a
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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