Rsu 1137 → alpha-(((2-Bromoethyl)amino)methyl)-2-nitro-1H-imidazole-1-ethanol hydrobromide (1:1)
Reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][CH:10]([OH:16])[CH2:11][NH:12][CH2:13][CH2:14]O)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[Br-:17].C[S+](C)[Br:20]>CN(C)C=O.[Ag]>[BrH:20].[N+:1]([C:4]1[N:5]([CH2:9][CH:10]([OH:16])[CH2:11][NH:12][CH2:13][CH2:14][Br:17])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]Participants
Conditions
- Temperature
- 50 °C
Procedure
A mixture containing 1-(2-nitro-1-imidazolyl)-3-(2-hydroxyethylamino)-2-propanol (RSU-1137) prepared as described by Silver et al. [Silver, A.R.J., McNeil, S.S., O'Neill, P., Jenkins, T.C. and Ahmed, I., Biochemical Pharmacology 1986 35 3923-3928] (2.30 g, 10.0 mmol) and dimethylbromo-sulphonium bromide (2.22 g, 10.0 mmol) prepared by the method of Furukawa et al. [Furukawa, N., Inoue, T., Aida, T. and Oae, S., J. Chem. Soc. Chem. Commun. 1973 212] in N,N-dimethylformamide (20 cm3) was stirred at 50° C. for 12 hours. The reaction mixture was concentrated in vacuo, digested in ethanol (10 cm3) and separated by preparative column chromatography using silica gel as the stationary phase and chloroform-methanol (9:1 v/v) as eluant. 1-(2-Nitro-1-imidazolyl)-3-(2-bromoethylamino)-2-propanol hydrobromide (0.68 g, 18.2%) was obtained as a yellow solid, m.p. 148.5°-150.5° C. after treatment of the eluate with ethereal hydrogen bromide.
Workup
- customprepared
- concentrationThe reaction mixture was concentrated in vacuo
- customseparated by preparative column chromatography
Sources & evidence
- ORD record
- ord-b1058e2384a94cc49af63de5856388e4
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05098921
Reaction notes
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