Ethanol → HCID 86742463, compound

HRID 867547Notes

Reaction equation

HRID 867547 reaction equation
C(O)C.[O:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]2[CH:16]=[N:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:8]2[C@@H:7]2[CH2:24][CH2:25][CH2:26][N:6]12.[OH-].[Na+].[C:29](=[N:32]O)([NH2:31])[CH3:30]>O.Cl.CN(C)C=O>[CH3:30][C:29]1[N:32]=[C:19]([C:18]2[N:17]=[CH:16][N:9]3[C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:5](=[O:4])[N:6]4[CH2:26][CH2:25][CH2:24][C@H:7]4[C:8]=23)[O:21][N:31]=1.[C:19]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:18]

Participants

8

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 30926N-HydroxyacetamidineHCID 10041121Ethyl (7S)-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate

Product 1

HCID 86742463HCID 86742463, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

40 ml of ethanol and 14.0 g (44.9 mmol) of ethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate are added to a solution of 2.21 g (55.2 mmol) of sodium hydroxide in 10 ml of water and the mixture is stirred at boiling temperature for 30 minutes. The mixture is diluted with 40 ml of water and neutralized with 13.8 ml of 4N hydrochloric acid. After evaporation of the ethanol in a water-jet vacuum the suspension is filtered; the filter residue is rinsed with water and dried at 90° in a high vacuum. The product obtained is suspended in 60 ml of N,N-dimethylformamide, 9.40 g (56 mmol) of N,N'-carbonyldiimidazole are added thereto and the mixture is stirred at 60° overnight. The reaction mixture is treated with 3.65 g (49.3 mmol) of acetamidoxime and stirred at 60° for a further 2 hours. The mixture is evaporated to dryness, the residue is dissolved in 50 ml of glacial acetic acid and the solution is heated to 120° for 2.5 hours. The yellow solution is concentrated; the residue is taken up in methylene chloride and washed with a saturated sodium bicarbonate solution. The organic phase is dried over magnesium sulphate, evaporated and there is obtained by recrystallization of the residue from methylene chloride and ethyl acetate (S)-11,12,13,13a-tetrahydro-1-(3-methyl-1,2,4-oxadiazol-5-yl)-9H-imidazo [1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 180°-182°.

Workup

  1. customfor 30 minutes
  2. customAfter evaporation of the ethanol in a water-jet vacuum the suspension
  3. filtrationis filtered
  4. washthe filter residue is rinsed with water
  5. customdried at 90° in a high vacuum
  6. customThe product obtained
  7. stirringthe mixture is stirred at 60° overnight
  8. stirringstirred at 60° for a further 2 hours
  9. customThe mixture is evaporated to dryness
  10. dissolutionthe residue is dissolved in 50 ml of glacial acetic acid
  11. temperaturethe solution is heated to 120° for 2.5 hours
  12. concentrationThe yellow solution is concentrated
  13. washwashed with a saturated sodium bicarbonate solution
  14. dry with materialThe organic phase is dried over magnesium sulphate
  15. customevaporated

Sources & evidence

ORD record
ord-7c3b41fb70c94bd4a82997f9f571395a
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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