N'-hydroxy-2-methoxyethanimidamide → 7-chloro-4,5-dihydro-3-(3-methoxymethyl-1,2,4-oxadiazol-5-yl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 867562Notes

Reaction equation

HRID 867562 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([N:18]3C=CN=C3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:25][O:26][CH2:27][C:28](=NO)[NH2:29]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][N:29]=[C:28]([CH2:27][O:26][CH3:25])[N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4126736N'-hydroxy-2-methoxyethanimidamideHCID 13987114HCID 13987114, compound

Product 1

HCID 212899767-chloro-4,5-dihydro-3-(3-methoxymethyl-1,2,4-oxadiazol-5-yl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.80 g (20 mmol) of 1-[[7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl]carbonyl]imidazole, 50 ml of N,N-dimethylformamide and 2.10 g (20 mmol) of methoxyacetamidoxime is stirred at 100° overnight. The solution is then evaporated and the residue is partitioned between methylene chloride and water. The organic phase is dried over magnesium sulphate and evaporated. By chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from methylene chloride and ethyl acetate there is obtained 7-chloro-4,5-dihydro-3-(3-methoxymethyl-1,2,4-oxadiazol-5-yl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 213°-215°.

Workup

  1. customThe solution is then evaporated
  2. customthe residue is partitioned between methylene chloride and water
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated
  5. washBy chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-11ab2045b2a9466091512c0681e45206
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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