Ammonia → 3-[-1-(3-mercaptopropyl)-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

HRID 345708Notes

Reaction equation

HRID 345708 reaction equation
C([S:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=2[C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)=[CH:9]1)(=O)C.N>CO.CN(C=O)C.[Cl-].[Na+]>[SH:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=2[C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)=[CH:9]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18780220HCID 18780220, compound

Product 1

HCID 187802793-[-1-(3-mercaptopropyl)-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dioneYield 83.7%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

350 mg of the product of Example 99 in 20 ml of 50% methanol/DMF were treated with 0.5 ml of 33% aqueous ammonia. The mixture was stirred for 17 hours, then diluted with 20 ml of sodium chloride solution and extracted with ethyl acetate. The ethyl acetate extracts were dried and evaporated. Chromatography of the residue on silica gel with ethyl acetate/hexane (3:1) gave 266 mg of 3-[-1-(3-mercaptopropyl)-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 155°-157° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-37108df2563341debcb98f50d7da69a7
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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