Dimethylformamide → HCID 69479382, compound

HRID 856299Notes

Reaction equation

[Cl: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.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.CN(C=O)C>O>[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]([CH3:14])([OH:12])[CH2:13][N:25]2[CH2:24][CH2:23][N:22]([C:19]3[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=3)[CH2:27][CH2:26]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

Conditions

Temperature: 72.5 °C

Procedure

(R)-2-Chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 12 (20 g, 91.9 mmol) and 1-(4-chlorophenyl)piperazine (20.8 g, 0.11 mol) were added to DMF (200 ml) followed by stirring at 70-75° C. for 5 hours. The reaction mixture was allowed to return to room temperature, poured into water, and extracted with ethyl acetate. The organic phase was washed with a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1) to afford (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-chlorophenyl)piperazin-1-yl]propan-2-ol (33.0 g, yield 87%) as a yellow amorphous form.

Workup

customto return to room temperature
extractionextracted with ethyl acetate
washThe organic phase was washed with a saturated saline solution
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1)

Sources & evidence

ORD record: ord-e9858f3a51cb474682f277e7ea6e5b66
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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