Water → 5-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-3-ylmethyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1378249Notes

Reaction equation

HRID 1378249 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].[CH3:13][N:14]1[C:20](=[O:21])[C:19]2[S:22][CH:23]=[CH:24][C:18]=2[N:17]2[CH:25]=[N:26][C:27]([C:28](O)=O)=[C:16]2[CH2:15]1.[OH2:31]>CN(C)C=O>[CH3:13][N:14]1[C:20](=[O:21])[C:19]2[S:22][CH:23]=[CH:24][C:18]=2[N:17]2[CH:25]=[N:26][C:27]([CH2:28][C:18]3[CH:19]=[C:20]4[C:11](=[CH:23][CH:24]=3)[C:12](=[O:31])[NH:8][C:1]4=[O:2])=[C:16]2[CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 212899275,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylic acid

Product 1

HCID 229142455-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-3-ylmethyl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.39 g (20 mmol) of 1,1'-carbonyldiimidazole were added in one portion at room temperature to a solution of 5.27 g (20 mmol) of 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylic acid in 50 ml of dimethylformamide and the mixture was stirred at 50° for 30 minutes. Subsequently, 4.47 g (20 mmol) of phthaloylglycinamide oxime were added in one portion and the mixture was stirred at 110° for 15 hours. The dimethylformamide was evaporated in a high vacuum and the residue obtained was treated with 150 ml of water. Extraction with methylene chloride (twice), drying with sodium sulfate, filtration and evaporation yielded a reddish residue, which was subsequently chromatographed (silica gel, methylene chloride/methanol 20:1). After recrystallization from acetonitrile there were obtained 4.21 g (47%) of 5-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-3-ylmethyl)-2,3-dihydro-1H-isoindole-1,3-dione as pale brown crystals of m.p. 245°-246°.

Workup

  1. stirringthe mixture was stirred at 110° for 15 hours
  2. customThe dimethylformamide was evaporated in a high vacuum
  3. customthe residue obtained
  4. extractionExtraction with methylene chloride (twice),
  5. dry with materialdrying with sodium sulfate, filtration and evaporation
  6. customyielded a reddish residue, which
  7. customwas subsequently chromatographed (silica gel, methylene chloride/methanol 20:1)
  8. customAfter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-39ca9f141e614335a3a19b5d315d09a7
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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