Dimethylformamide → 2-Methyl-6-nitro-2-[4-(4-trifluoromethylbenzoyl)piperidin-1-yl]methyl-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856250

반응식

HRID 856250 반응식
Cl[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:32])([F:31])[C:17]1[CH:30]=[CH:29][C:20]([C:21]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1.C([O-])(=O)C.[Na+].CN(C=O)C>O>[CH3:14][C:11]1([CH2:13][N:26]2[CH2:25][CH2:24][CH:23]([C:21](=[O:22])[C:20]3[CH:29]=[CH:30][C:17]([C:16]([F:31])([F:32])[F:15])=[CH:18][CH:19]=3)[CH2:28][CH2:27]2)[O:12][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 116374554-(4-Trifluoromethylbenzoyl)piperidineHCID 159655232-Chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole

생성물 1

HCID 694830932-Methyl-6-nitro-2-[4-(4-trifluoromethylbenzoyl)piperidin-1-yl]methyl-2,3-dihydroimidazo[2,1-b]oxazole수율 29%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 6 (80 mg, 0.37 mmol), 4-(4-trifluoromethylbenzoyl)piperidine (95 mg, 0.37 mmol), sodium acetate (150 mg, 1.83 mmol) and DMF (2 ml) was stirred at 80° C. overnight. The reaction mixture was poured into water, and extracted with ethyl acetate twice. The organic phases were combined, washed with water three times, washed with a saturated saline solution, dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/1) to afford 2-methyl-6-nitro-2-[4-(4-trifluoromethylbenzoyl)piperidin-1-yl]methyl-2,3-dihydroimidazo[2,1-b]oxazole (46 mg, yield 29%) as a white powder.

후처리

  1. extractionextracted with ethyl acetate twice
  2. washwashed with water three times
  3. washwashed with a saturated saline solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/1)

출처 및 근거

ORD 기록
ord-20cf7a1eeea74674948a0059cc2514ee
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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