Water → HCID 56627668, compound

HRID 1606962Notes

Reaction equation

HRID 1606962 reaction equation
Cl[C:2]1[C:7]2[C:8](=O)[N:9]3CC[C@H:10]3[C:11]3[N:12](C=NC=3/C=C\Cl)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[OH2:33]>CN(C)C=O>[N:12]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]2[C:6]=1[C:5](=[O:33])[CH:4]=[CH:3][CH:2]=2

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86743359HCID 86743359, compound

Product 1

HCID 56627668HCID 56627668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.21 g (6.9 mmol) of (S)-8-chloro-1-[(Z)-2-chlorovinyl]-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one was heated to boiling under reflux for 4 hours together with 1.23 ml (8.3 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 30 ml of N,N-dimethylformamide. The reaction mixture was subsequently poured into 300 ml of water and extracted five times with methylene chloride. The organic extracts were washed four times with water, dried over magnesium sulphate and evaporated. After chromatography on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate there was obtained (S)-8-chloro-1-ethynyl-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4benzodiazepin-9-one of melting point 249°-250°.

Workup

  1. extractionextracted five times with methylene chloride
  2. washThe organic extracts were washed four times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. washAfter chromatography on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-040911eefe6c4ef0940586cf00d652c0
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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