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

HRID 863673Notes

Reaction equation

HRID 863673 reaction equation
[CH3:1][S:2]([O: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: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:4])=[O:3].[NH2:37][C:38]([NH2:40])=[S:39]>CN(C)C=O>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:38]([S: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)(=[NH:37])[NH2:40]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 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 196963983-[8-[(amidinothio)methyl]-6,7,8,9-tetrahydropyrido[1,2-a]-indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione methanesulfonateYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg of the pyrroledione product of Example 6 and 75 mg of thiourea in 5 ml of dimethylformamide was heated to 80° C. under a nitrogen atmosphere for 18 hours. The solvent was removed by evaporation and the residue was purified by chromatography on silica gel with dichloromethane/methanol/acetic acid/water (90:18:3:2). The residue was triturated with ethyl acetate to give 80 mg of 3-[8-[(amidinothio)methyl]-6,7,8,9-tetrahydropyrido[1,2-a]-indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione methanesulfonate of melting point 200°-205° C.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was purified by chromatography on silica gel with dichloromethane/methanol/acetic acid/water (90:18:3:2)
  3. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-83a63d5c56f64caaa090c6ef00c2b102
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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