1,1'-Carbonyldiimidazole → (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one

HRID 1378001Notes

Reaction equation

HRID 1378001 reaction equation
[CH2:1]([N:4]([CH2:9][CH:10]=[CH2:11])[CH2:5][C:6]([OH:8])=O)[CH:2]=[CH2:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[F:24][C:25]1[CH:26]=[CH:27][C:28]2[N:34]3[CH:35]=[N:36][C:37]([C:38](=[N:40]O)[NH2:39])=[C:33]3[C@@H:32]3[CH2:42][CH2:43][N:31]3[C:30](=[O:44])[C:29]=2[CH:45]=1>CN(C)C=O>[CH2:9]([N:4]([CH2:5][C:6]1[O:8][N:40]=[C:38]([C:37]2[N:36]=[CH:35][N:34]3[C:28]4[CH:27]=[CH:26][C:25]([F:24])=[CH:45][C:29]=4[C:30](=[O:44])[N:31]4[CH2:43][CH2:42][C@H:32]4[C:33]=23)[N:39]=1)[CH2:1][CH:2]=[CH2:3])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 20458556DiallylglycineHCID 54513121(S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto-[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime

Product 1

HCID 54559715(S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-oneYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.32 g (15 mmol) of diallylglycine were dissolved in 15 ml of N,N-dimethylformamide and treated with 2.75 g (17 mmol) of 1,1'-carbonyldiimidazole. After stirring at 50° C. for 20 minutes 3.01 (10 mmol) of (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime were added and the mixture was stirred at 90° for 16 hours and at 120° for 2 hours. The solution was concentrated and the residue was purified by chromatography on 320 g of silica gel while eluting with ethyl acetate. There were obtained 1.54 g (37%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 100°-105°.

Workup

  1. additionwere added
  2. concentrationThe solution was concentrated
  3. customthe residue was purified by chromatography on 320 g of silica gel
  4. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-580e27c33ec845ceae9f6659ce2c08e9
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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