Ammonia → HCID 53911072, compound

HRID 1378062Notes

Reaction equation

HRID 1378062 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[F:13][C:14]1[CH:15]=[CH:16][C:17]2[N:23]3[CH:24]=[N:25][C:26]([C:27](O)=[O:28])=[C:22]3[C@@H:21]3[CH2:30][CH2:31][CH2:32][N:20]3[C:19](=[O:33])[C:18]=2[C:34]=1[F:35].N>CN(C)C=O>[F:13][C:14]1[CH:15]=[CH:16][C:17]2[N:23]3[CH:24]=[N:25][C:26]([C:27]([NH2:3])=[O:28])=[C:22]3[C@@H:21]3[CH2:30][CH2:31][CH2:32][N:20]3[C:19](=[O:33])[C:18]=2[C:34]=1[F:35]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 53891595HCID 53891595, compound

Product 1

HCID 53911072HCID 53911072, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.1 g (37.9 mmol) of 1,1'-carbonyldiimidazole were added portionwise to a suspension of 11 g (34.5 mmol) of (S)-7,8-difluoro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid in 80 ml of dimethylformamide. The resulting pale brown solution was heated to 50° for 45 minutes. The solution was subsequently cooled to room temperature and 12 ml of aqueous ammonia solution were added dropwise. After stirring for a further 30 minutes the reaction mixture was poured into 150 ml of ice-water and extracted seven times with methylene chloride. Drying of the organic phases with sodium sulfate, filtration and evaporation yielded a colourless residue which was triturated with methylene chloride. After drying in a high vacuum there were obtained 9.8 g of (S)-7,8-difluoro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide m.p. 221°-224°.

Workup

  1. temperatureThe resulting pale brown solution was heated to 50° for 45 minutes
  2. extractionextracted seven times with methylene chloride
  3. dry with materialDrying of the organic phases with sodium sulfate, filtration and evaporation
  4. customyielded a colourless residue which
  5. customwas triturated with methylene chloride
  6. customAfter drying in a high vacuum there

Sources & evidence

ORD record
ord-60e42305e49e4fb4881ccccaf82570cb
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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