Triethylamine → (S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]-(4-trifluoromethylphenyl)methanone

HRID 856321노트

반응식

HRID 856321 반응식
Cl.Cl.[CH3:3][C@@:4]1([CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[O:8][C:7]2=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]2[CH2:5]1.C(N(CC)CC)C.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:3][C@@:4]1([CH2:15][N:16]2[CH2:17][CH2:18][N:19]([C:35]([C:34]3[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:40])[F:41])=[CH:39][CH:38]=3)=[O:36])[CH2:20][CH2:21]2)[O:8][C:7]2=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]2[CH2:5]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 69481767(S)-2-methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride

생성물 1

HCID 69481599(S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]-(4-trifluoromethylphenyl)methanone수율 68.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-2-Methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride prepared in Example 408 (2.36 mg, 0.882 mmol) was suspended in methylene chloride (10 ml). To the suspension, triethylamine (1 ml, 7.17 mmol) was added. To the solution, 4-(trifluoromethyl)benzoyl chloride (193 mg, 0.926 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 1 hour. The reaction mixture was washed with a saturated sodium hydrogencarbonate solution, water and a saturated saline solution in this order, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford (S)-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]-(4-trifluoromethylphenyl)methanone (264 mg, yield 68%) as a white powder.

후처리

  1. temperaturewith cooling on ice-bath
  2. washThe reaction mixture was washed with a saturated sodium hydrogencarbonate solution, water
  3. dry with materiala saturated saline solution in this order, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

출처 및 근거

ORD 기록
ord-79809ccc713545758f4e51d5e365dc35
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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