Dimethylformamide → 5,6-dihydro-5-methyl-3-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378050Notes

Reaction equation

HRID 1378050 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]([OH:19])=O)=[C:4]2[CH2:3]1.C([N:27]1C=C[N:29]=[CH:28]1)(N1C=CN=C1)=O.F[C:33](F)(F)[C:34]([OH:36])=O.[CH3:39][N:40](C)[CH:41]=[O:42]>>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]3[O:19][N:27]=[C:28]([CH2:39][N:40]4[C:34](=[O:36])[C:33]5=[CH:8][CH:7]=[CH:6][CH:13]=[C:12]5[C:41]4=[O:42])[N:29]=3)=[C:4]2[CH2:3]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 103326765-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid

Product 1

HCID 229143775,6-dihydro-5-methyl-3-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 50%

Procedure

15 g (5.83 mmol) of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]-[1,4]benzodiazepine-3-carboxylic acid were dissolved in 100 ml of N,N-dimethylformamide, treated portionwise with 11.3 g (7 mmol) of 1,1'-carbonyldiimidazole and stirred at 70° for 20 min. After adding 19.2 g (8.75 mmol) of phthaloylglycine amidoxime the mixture was stirred at 80° for 3 hours, 5 ml of trifluoroacetic acid were added and the mixture was stirred at 110° overnight. The reaction mixture was concentrated and the residue was chromatographed on 200 g of silica gel while eluting with ethyl acetate. There were obtained 13 g (50%) of 5,6-dihydro-5-methyl-3-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 239°-240°.

Workup

  1. stirringwas stirred at 80° for 3 hours
  2. stirringthe mixture was stirred at 110° overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was chromatographed on 200 g of silica gel
  5. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-b373ddd97dd84a2982f31258659ab85a
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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