Dichloromethane → HCID 86751231, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[O:5][N:4]=1.C(N(C(C)C)[CH:28]([CH3:30])[CH3:29])C.[CH2:34](Br)[C:35]#[CH:36].C(Cl)[Cl:39]>>[ClH:39].[CH2:30]([C:2]([CH2:36][C:35]#[CH:34])([NH2:1])[C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[O:5][N:4]=1)[C:28]#[CH:29]Participants
Procedure
328 mg (1.0 mmol) of 3-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-fluoro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 6 ml of methylene chloride were treated under argon with 1.2 ml (7.0 mmol) of N-ethyldiisopropylamine and 0.65 ml (6.0 mmol) of propargyl bromide (80% in toluene) and the mixture was stirred at room temperature under argon for 19 hrs. The solution was washed with 10 ml of water and evaporated, and the crude product was purified by chromatography on 15 g of silica gel (methylene chloride/acetone 9:1). The eluate was evaporated and the residue was taken up in 5 ml of methanol. The solution was acidified with 5 ml of ethereal hydrochloric acid and the white crystals were filtered off. There were obtained 200 mg (45%) of 3-[3-[bis-(prop-2-ynyl)-aminomethyl]-1,2,4-oxadiazol-5-yl]-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride (4:5) of m.p. 186°-189° (dec.).
Workup
- washThe solution was washed with 10 ml of water
- customevaporated
- customthe crude product was purified by chromatography on 15 g of silica gel (methylene chloride/acetone 9:1)
- customThe eluate was evaporated
- filtrationthe white crystals were filtered off
Sources & evidence
- ORD record
- ord-524dabdd553d4f27b02680ef652a9fc6
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665718
Reaction notes
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