Ammonia → HCID 54132851, compound

HRID 1418932Notes

Reaction equation

HRID 1418932 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 g (0.715 mol) 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 dimethylformamide, treated at room temperature with 116 g (0.715 mol) of carbonyldiimidazole and stirred at 50° for 1/2 hr. Then, 173 ml of 25% ammonia were added dropwise at 25°-30° within 1/2 hr. After stirring for 1/2 hr the reaction mixture was concentrated and the residue was dissolved in 500 ml of alcohol. After the addition of 250 ml of ether the solution was cooled to 0° and the suspension was suction filtered. 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; m.p. 228°-230°.

Workup

  1. stirringAfter stirring for 1/2 hr the reaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe residue was dissolved in 500 ml of alcohol
  4. additionAfter the addition of 250 ml of ether the solution
  5. temperaturewas cooled to 0°
  6. filtrationfiltered

Sources & evidence

ORD record
ord-4282728d002c4886b9b538a963992684
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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