Acetone → HCID 22914446, compound

HRID 1378234Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]3[CH:13]=[N:14][C:15](C4N=C(CN(CC)CC)ON=4)=[C:11]3[CH2:10][N:9]([CH3:27])[C:8](=[O:28])[C:7]=2[CH:29]=1.[CH3:30][C:31](C)=[O:32]>>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]3[C:13]([C:13]4[N:14]=[C:31]([CH2:30][N:9]([CH2:10][CH3:11])[CH2:8][CH3:7])[O:32][N:12]=4)=[N:14][CH:15]=[C:11]3[CH2:10][N:9]([CH3:27])[C:8](=[O:28])[C:7]=2[CH:29]=1

Participants

Reactant 3

HCID 180Acetone

HCID 313Hydrochloric Acid

HCID 22914364HCID 22914364, compound

Product 1

HCID 22914446HCID 22914446, compoundYield 42%

Procedure

A solution of 200 mg (0.54 mmol) of 8-chloro-3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 4 ml of N,N-dimethylformamide was treated with 0.17 ml (1.65 mmol) of diethylamine and stirred at room temperature under argon for 1.5 hrs. The solution was evaporated and the residue was triturated in 10 ml of water. The crystals were filtered off under suction, the filtrate was extracted once with ethyl acetate and the extract was evaporated. The combined crude products were chromatographed on 20 g of silica gel (methylene chloride/acetone 4:1, 2:1). There were obtained 124 mg of 8-chloro-3-(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted in acetone with ethereal hydrochloric acid into the hydrochloride. By crystallization from acetonitrile there were obtained 108 mg (42%) of 8-chloro-1-(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride (1:1.9) of m.p. 191°-205° (dec.).

Workup

customBy crystallization from acetonitrile

Sources & evidence

ORD record: ord-af5add2a0c9e4ae89db6fe852b2ec36c
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665718

Reaction notes

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