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

HRID 1378146Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19](CCl)[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27].[CH3:31]N(C)C=O>>[Cl:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH:16]3[N:20]=[C:19]([N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])[O:18][N:17]3[CH3:31])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 8021Diethylamine

HCID 53954665(S)-8-chloro-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one

Product 1

HCID 70090142(S)-8-chloro-1-(5-diethylamino-methyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-oneYield 96%

Procedure

3.76 g (10 mmol) of (S)-8-chloro-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were stirred at room temperature overnight with 2.19 g (30 mmol) of diethylamine and 30 ml of N,N-dimethylformamide. By evaporation of the reaction mixture and chromatography of the residue on silica gel while eluting with methylene chloride/methanol 19/1 there were obtained 4.5 g (96%) of (S)-8-chloro-1-(5-diethylamino-methyl-1,2,4-oxadiazol-3-yl)-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. 218°-220°.

Workup

customBy evaporation of the reaction mixture and chromatography of the residue on silica gel
washwhile eluting with methylene chloride/methanol 19/1 there

Sources & evidence

ORD record: ord-3d678dd6d62f4cd7b6581f20885c623d
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665718

Reaction notes

Loading…