Ammonia → HCID 54132851, compound

HRID 1378135Notes

Reaction equation

HRID 1378135 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([OH:18])=O)=[C:5]2[C@@H:4]2[CH2:19][CH2:20][N:3]12.C(N1C=CN=C1)([N:23]1C=CN=C1)=O.N>CN(C)C=O>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([NH2:23])=[O:18])=[C:5]2[C@@H:4]2[CH2:19][CH2:20][N:3]12

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 54232542HCID 54232542, compound

Product 1

HCID 54132851HCID 54132851, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

192.4 g (714.6 mmol) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid were suspended in 900 ml of N,N-dimethylformamide, treated at room temperature with 116 g (715 mmol) of 1,1'-carbonyldiimidazole and stirred at 50° for 30 minutes. 173 ml of 25% ammonia were added dropwise at 25°-30° within 30 minutes. After stirring for 30 minutes the reaction mixture was concentrated and the residue was dissolved in 500 ml of alcohol. After adding 250 ml of ether the mixture was cooled to 0° and the crystallizate was filtered off under suction and dried. There were obtained 133.6 g (69%) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide of m.p. 228°-230°.

Workup

  1. stirringAfter stirring for 30 minutes the reaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe residue was dissolved in 500 ml of alcohol
  4. additionAfter adding 250 ml of ether the mixture
  5. temperaturewas cooled to 0°
  6. filtrationthe crystallizate was filtered off under suction
  7. customdried

Sources & evidence

ORD record
ord-a74f2ce626654a2d857b806279df6c37
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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