Water → HCID 54397252, compound

HRID 1606964Notes

Reaction equation

HRID 1606964 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3/[CH:16]=[CH:17]\Cl)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[CH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86743360HCID 86743360, compound

Product 1

HCID 54397252HCID 54397252, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g (7.5 mmol) of (S)-8-chloro-1-[(Z)-2-chlorovinyl]-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one was heated to boiling under reflux for 5 hours together with 1.66 ml (11.2 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 400 ml of water and the crystals obtained were filtered off. After drying and recrystallization from N,N-dimethylformamide there was obtained (S)-8-chloro-1-ethynyl-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 324°-325°.

Workup

  1. customthe crystals obtained
  2. filtrationwere filtered off
  3. customAfter drying
  4. customrecrystallization from N,N-dimethylformamide

Sources & evidence

ORD record
ord-2bfecee28e7d499f977d707fd4376858
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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