Dimethylformamide → HCID 53920921, compound

HRID 1154482Notes

Reaction equation

HRID 1154482 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](N3C=CN=C3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[OH:40].CN(C)C=O>O>[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:40][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[Cl:33])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 54332091(S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole

Product 1

HCID 53920921HCID 53920921, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0 g (8.2 mmol) of 1-[[(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[ 2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole, 1.59 g (11.5 mmol) of powdered potassium carbonate, 1.3 ml (11.5 mmol) of 2-chlorophenol and 20 ml of dry dimethylformamide is stirred at room temperature for 5 days, then poured into 60 ml of water and extracted three times with methylene chloride. The organic extracts are washed twice with saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The crude product is chromatographed on silica gel, the elution being carried out successively with ethyl acetate/n-hexane (1:1), ethyl acetate/n-hexane (3:2) and ethyl acetate/n-hexane (7:3). After recrystallization from ethyl acetate, there is obtained o-chlorophenyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 214°-215°.

Workup

  1. extractionextracted three times with methylene chloride
  2. washThe organic extracts are washed twice with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is chromatographed on silica gel
  6. washthe elution
  7. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b435665d6b2b4e2b8553ee2e3ee756bf
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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