Dimethylformamide → HCID 54568419, compound

HRID 1154485Notes

Reaction equation

HRID 1154485 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+].[CH3:33][O:34][C:35]1[CH:41]=[CH:40][CH:39]=[C:37]([OH:38])[CH:36]=1.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:38][C:37]3[CH:39]=[CH:40][CH:41]=[C:35]([O:34][CH3:33])[CH:36]=3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 90073-MethoxyphenolHCID 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 54568419HCID 54568419, 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, 1.43 g (11.5 mmol) of resorcinol monomethyl ether and 20 ml of dry dimethylformamide is stirred at room temperature for 2 days, then poured into 60 ml of water and extracted three times with methylene chloride. The organic extracts are washed once with saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The residue obtained is chromatographed on silica gel while eluting with ethyl acetate/n-hexane (3:1) and subsequently crystallized from ethyl acetate. There is obtained m-methoxyphenyl (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 184°-185°.

Workup

  1. extractionextracted three times with methylene chloride
  2. washThe organic extracts are washed once with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis chromatographed on silica gel
  7. washwhile eluting with ethyl acetate/n-hexane (3:1)
  8. customsubsequently crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ba375e5a704d4e489fedb54b4f89b1e6
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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