Dimethylformamide → HCID 22914227, compound
Reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([OH:18])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([N:28]1C=C[N:30]=[CH:29]1)(N1C=CN=C1)=O.F[C:34](F)(F)[C:35]([OH:37])=O.[CH3:40][N:41](C)[CH:42]=[O:43]>>[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:18][N:28]=[C:29]([CH2:40][N:41]4[C:35](=[O:37])[C:34]5=[CH:4][CH:3]=[CH:2][CH:7]=[C:6]5[C:42]4=[O:43])[N:30]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
Procedure
38.8 g (133 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]-benzodiazepine-3-carboxylic acid were dissolved in 200 ml of N,N-dimethylformamide, treated portionwise with 23.7 g (146 mmol) of 1,1'-carbonyldiimidazole and stirred at 70° for 20 min. After adding 43.73 g (199.5 mmol) of phthaloylglycine amidoxime the mixture was stirred at 90° for 1 hour. 1.5 ml of trifluoroacetic acid were added and the mixture was stirred at 90° overnight and at 120° for a further 3 hours. The suspension obtained was concentrated to half of its volume and cooled, and the precipitated crystals were filtered off. There were obtained 35.3 g (56%) of 7-chloro-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. 237°-239°.
Workup
- stirringwas stirred at 90° for 1 hour
- stirringthe mixture was stirred at 90° overnight and at 120° for a further 3 hours
- customThe suspension obtained
- concentrationwas concentrated to half of its volume
- temperaturecooled
- filtrationthe precipitated crystals were filtered off
Sources & evidence
- ORD record
- ord-d985aac4815d4ad691e9b3f728e4b553
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665718
Reaction notes
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