(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole → (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-{4-[(4-trifluoromethylbenzylidene)amino]piperazin-1-yl}propan-2-ol

HRID 856338ノート

反応式

HRID 856338 の反応式
[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.[N:15]1([N:21]=[CH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>CN(C=O)C>[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]([CH3:14])([OH:12])[CH2:13][N:18]2[CH2:17][CH2:16][N:15]([N:21]=[CH:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:27][CH:28]=3)[CH2:20][CH2:19]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

参加物

4

反応物 2

HCID 10443353(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleHCID 69481693Piperazin-1-yl-(4-trifluoromethylbenzylidene)-amine

生成物 1

HCID 69481568(S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-{4-[(4-trifluoromethylbenzylidene)amino]piperazin-1-yl}propan-2-ol収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

A mixture of (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 12 (218 mg, 1 mmol), N-(piperazin-1-yl)-N-(4-trifluoromethylbenzylidene)amine (283 mg, 1.1 mmol) and DMF (2 ml) was stirred at 70-80° C. for 7 hours. The reaction mixture was allowed to return to room temperature and then added water, and the resulting solution was extracted with ethyl acetate twice. The organic phases were combined, washed with water 3 times and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/acetone=1/1) to afford (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-{4-[(4-trifluoromethylbenzylidene)amino]piperazin-1-yl}propan-2-ol (402 mg, yield 85%) as a light yellow powder.

後処理

  1. customto return to room temperature
  2. extractionadded water, and the resulting solution was extracted with ethyl acetate twice
  3. washwashed with water 3 times
  4. dry with materiala saturated saline solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane/acetone=1/1)

出典と根拠

ORDレコード
ord-4ed393e1b33e4c0aa18c4ec9589602ba
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

反応ノート

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