Dimethylformamide → HCID 54518764, compound

HRID 867546Notes

Reaction equation

HRID 867546 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15](O)=[O:16])=[C:10]3[C@@H:9]3[CH2:18][CH2:19][CH2:20][N:8]3[C:7](=[O:21])[C:6]=2[CH:22]=1.CN(C)C=O.[C:28](=[N:31]O)([NH2:30])[CH3:29]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[O:16][N:31]=[C:28]([CH3:29])[N:30]=4)=[C:10]3[C@@H:9]3[CH2:18][CH2:19][CH2:20][N:8]3[C:7](=[O:21])[C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 30926N-HydroxyacetamidineHCID 54510081HCID 54510081, compound

Product 1

HCID 54518764HCID 54518764, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.60 g (28.5 mmol) of (S)-7-fluoro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid, 30 ml of N,N-dimethylformamide and 6.16 g (38 mmol) of N,N'-carbonyldiimidazole are stirred at room temperature for 45 minutes and at 55° for 1 hour. 2.44 g (33 mmol) of acetamidoxime are subsequently added and the mixture is stirred at 75° for a further 1.5 hours. The mixture is poured into 200 ml of water, stirred for 20 minutes, suction filtered and the filter residue is dried. 8.60 g of the thus-obtained product are stirred at 115° for 2.5 hours in 50 ml of glacial acetic acid. The solution is evaporated and the residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic phase is separated, dried over magnesium sulphate and evaporated. By recrystallization of the residue from ethyl acetate there is obtained (S)-7-fluoro-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 248°-249°.

Workup

  1. stirringstirred for 20 minutes
  2. filtrationsuction filtered
  3. customthe filter residue is dried
  4. stirring8.60 g of the thus-obtained product are stirred at 115° for 2.5 hours in 50 ml of glacial acetic acid
  5. customThe solution is evaporated
  6. customthe residue is partitioned between methylene chloride and saturated sodium bicarbonate solution
  7. customThe organic phase is separated
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customBy recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-dba9ed61dcfd42d6a4479f15096a91d8
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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