1,1'-Carbonyldiimidazole → (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

HRID 1377986Notes

Reaction equation

HRID 1377986 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.[Cl:24][C:25]1[C:30]2[C:31](=[O:45])[N:32]3[CH2:44][CH2:43][C@H:33]3[C:34]3[N:35]([CH:36]=[N:37][C:38]=3[C:39](=[N:41]O)[NH2:40])[C:29]=2[CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[CH2:9]([N:4]([CH2:5][C:6]1[O:8][N:41]=[C:39]([C:38]2[N:37]=[CH:36][N:35]3[C:29]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:24])[C:30]=4[C:31](=[O:45])[N:32]4[CH2:44][CH2:43][C@H:33]4[C:34]=23)[N:40]=1)[CH2:1][CH:2]=[CH2:3])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 20458556DiallylglycineHCID 54137540(S)-8-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime

Product 1

HCID 54478237(S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-oneYield 49.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

36.5 g (235 mmol) of diallylglycine were dissolved in 165 ml of N,N-dimethylformamide and treated portionwise with 40.5 g (250 mmol) of 1,1'-carbonyldiimidazole. After stirring for 10 minutes 40 g (126 mmol) of (S)-8-chloro-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 room temperature for 1 hour and at 110° for 3.5 hours. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel while eluting with methylene chloride/ethyl acetate 1/1. There were obtained 27.1 g (45%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-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. 181°-182.5°.

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by chromatography on silica gel
  4. washwhile eluting with methylene chloride/ethyl acetate 1/1

Sources & evidence

ORD record
ord-d6b007780d02427f834ed6b9160c5e4f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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