Ammonia → HCID 53829958, compound

HRID 1378015Notes

Reaction equation

HRID 1378015 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[C:8]2[C:9](=[O:22])[N:10]3[CH2:21][CH2:20][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17]([OH:19])=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N1C=CN=C1)([N:27]1C=CN=C1)=O.C(=O)=O.N>CN(C)C=O>[F:24][C:2]([F:23])([F:1])[C:3]1[C:8]2[C:9](=[O:22])[N:10]3[CH2:21][CH2:20][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17]([NH2:27])=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 22821779HCID 22821779, compound

Product 1

HCID 53829958HCID 53829958, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g (29.7 mmol) of (S)-8-trifluoromethyl-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid were suspended in 50 ml of N,N-dimethylformamide and treated portionwise at room temperature with 5.1 g (31.2 mmol) of 1,1'-carbonyldiimidazole. After completion of the CO2 evolution the clear brown solution was stirred at 50° for 20 min., cooled and treated dropwise with 8 ml of conc. ammonia at a temperature below 150 within about 15'. After stirring for 40 minutes the suspension obtained was poured into 300 ml of ice-water, whereupon the mixture was stirred at room temperature for 20', filtered and rinsed with a small amount of water. After drying there were obtained 7.51 g (75%) of (S)-8-trifluoromethyl-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide of m.p. >300°.

Workup

  1. temperaturecooled
  2. customobtained
  3. stirringwas stirred at room temperature for 20',
  4. filtrationfiltered
  5. washrinsed with a small amount of water
  6. customAfter drying there

Sources & evidence

ORD record
ord-7605d2b06593443c9a12fc2dda91c528
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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