Ammonia → HCID 22914318, compound

HRID 1378125Notes

Reaction equation

HRID 1378125 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH3:13][N:14]1[C:20](=[O:21])[C:19]2[CH:22]=[CH:23][S:24][C:18]=2[N:17]2[CH:25]=[N:26][C:27]([C:28]([OH:30])=O)=[C:16]2[CH2:15]1.N>CN(C)C=O>[CH3:13][N:14]1[C:20](=[O:21])[C:19]2[CH:22]=[CH:23][S:24][C:18]=2[N:17]2[CH:25]=[N:26][C:27]([C:28]([NH2:3])=[O:30])=[C:16]2[CH2:15]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 21289923HCID 21289923, compound

Product 1

HCID 22914318HCID 22914318, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.5 g (71 mmol) of 1,1'-carbonyldiimidazole were added portionwise to a suspension of 17 g (64.6 mmol) of 5-methyl-4-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepin-7-carboxylic acid (EP 285 837 A1)in 100 ml of N,N-dimethylformamide. The resulting pale brown solution was heated to 50° during 45 minutes. Subsequently, the solution was cooled to room temperature and 20 ml of aqueous ammonia solution were added dropwise thereto. After stirring for a further 30 minutes the reaction mixture was poured into 100 ml of ice-water and the resulting precipitate was filtered off and rinsed with water, ethanol and subsequently with ether. After drying at 70°/10 Torr there were obtained 15 g (89%) of 5-methyl-4-oxo-5,6-dihydro-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepine-7-carboxamide as colourless crystals of m.p. >250°.

Workup

  1. temperatureThe resulting pale brown solution was heated to 50° during 45 minutes
  2. filtrationthe resulting precipitate was filtered off
  3. washrinsed with water, ethanol and subsequently with ether
  4. customAfter drying at 70°/10 Torr there

Sources & evidence

ORD record
ord-c1605b8b011a4ec8a9a99189e7dea222
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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