(R)-2-bromo-4-nitro-1-(2-methyl-2-oxiranylmethyl)imidazole → (S)-1-(2-bromo-4-nitroimidazol-1-yl)-2-methyl-3-{4-[1-(4-trifluoromethoxyphenyl)piperidin-4-yl]piperazin-1-yl}propan-2-ol

HRID 856379Notes

Reaction equation

[Br:1][C:2]1[N:3]([CH2:10][C@:11]2([CH3:14])[CH2:13][O:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[F:15][C:16]([F:37])([F:36])[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][CH:27]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C(O)C>[Br:1][C:2]1[N:3]([CH2:10][C@@:11]([CH3:14])([OH:12])[CH2:13][N:33]2[CH2:34][CH2:35][N:30]([CH:27]3[CH2:26][CH2:25][N:24]([C:21]4[CH:20]=[CH:19][C:18]([O:17][C:16]([F:37])([F:15])[F:36])=[CH:23][CH:22]=4)[CH2:29][CH2:28]3)[CH2:31][CH2:32]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (R)-2-bromo-4-nitro-1-(2-methyl-2-oxiranylmethyl)imidazole (485 mg, 1.75 mmol), 1-[1-(4-trifluoromethoxyphenyl)piperidin-4-yl]piperazine (720 mg, 2.19 mmol) and ethanol (10 ml) was stirred at 50° C. for 8 hours. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to obtain (S)-1-(2-bromo-4-nitroimidazol-1-yl)-2-methyl-3-{4-[1-(4-trifluoromethoxyphenyl)piperidin-4-yl]piperazin-1-yl}propan-2-ol (792 mg, yield 77%) as a yellow amorphous form.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Sources & evidence

ORD record: ord-ca96ec7384af45bcab85837007ef9649
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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