Ammonia → HCID 54419029, compound

HRID 1378243Notes

Reaction equation

HRID 1378243 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[O:13]=[C:14]1[N:20]2[CH2:21][CH2:22][CH2:23][C@H:19]2[C:18]2=[C:24]([C:27]([OH:29])=O)[N:25]=[CH:26][N:17]2[C:16]2[CH:30]=[CH:31][S:32][C:15]1=2.N>CN(C)C=O>[O:13]=[C:14]1[N:20]2[CH2:21][CH2:22][CH2:23][C@H:19]2[C:18]2=[C:24]([C:27]([NH2:3])=[O:29])[N:25]=[CH:26][N:17]2[C:16]2[CH:30]=[CH:31][S:32][C:15]1=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 53828729HCID 53828729, compound

Product 1

HCID 54419029HCID 54419029, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.33 g (76 mmol) of 1,1'-carbonyldiimidazole were added portionwise to a suspension of 22 g (76 mmol) of (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxylic acid (EP 59 390 A1) in 100 ml of dimethylformamide. The resulting pale brown solution was heated to 50° for 45 minutes. Subsequently, the solution was cooled to room temperature and 14 ml of aqueous ammonia solution were added dropwise thereto. After 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 20 g (91%) of (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxamide as colourless crystals of m.p. 222°-223°.

Workup

  1. temperatureThe resulting pale brown solution was heated to 50° for 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-c7810c57eea34a959ab2f12f09980e7a
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…