Dimethylformamide → HCID 53739287, compound

HRID 1378031Notes

Reaction equation

HRID 1378031 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16](O)=[O:17])=[C:5]2[C@@H:4]2[CH2:19][CH2:20][N:3]12.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]>>[C:42]1(=[O:43])[N:41]([CH2:40][C:29]2[N:28]=[C:16]([C:15]3[N:14]=[CH:13][N:6]4[C:7]5[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=5[C:2](=[O:1])[N:3]5[CH2:20][CH2:19][C@H:4]5[C:5]=34)[O:17][N:30]=2)[C:35](=[O:37])[C:34]2=[CH:15][CH:5]=[CH:4][CH:19]=[C:20]12

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 54232542HCID 54232542, compound

Product 1

HCID 53739287HCID 53739287, compoundYield 40%

Procedure

13.46 g (50 mmol) of (S)-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxylic acid were dissolved in 40 ml of N,N-dimethylformamide, treated portionwise with 10 g (61.7 mmol) of 1,1'-carbonyldiimidazole and stirred at 55° for 30 min. After adding 12.06 g (55 mmol) of phthaloylglycine amidoxime the mixture was stirred at 85 °for 2 hours. 10 ml of trifluoroacetic acid were added and the mixture was stirred at 85 °overnight. The reaction mixture was cooled to 10 °and the crystals were filtered off. After recrystallization from methanol there were obtained 9.16 g (40%) of (S)-12,12a-dihydro-1-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepin-9-one of m.p. 290°-292°.

Workup

  1. stirringwas stirred at 85 °for 2 hours
  2. stirringthe mixture was stirred at 85 °overnight
  3. temperatureThe reaction mixture was cooled to 10
  4. filtrationthe crystals were filtered off
  5. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-2f6e3ef0a1a148b6bc151270b20ff188
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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