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

HRID 856333
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HRID 856333 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(=O)([O-])[O-].[K+].[K+].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH2:36][CH2:37][N:38]([C:41](Cl)=[O:42])[CH2:39][CH:40]=2)=[CH:31][CH:30]=1.O>CN(C=O)C>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH2:40][CH2:39][N:38]([C:41]([N:19]3[CH2:18][CH2:17][N:16]([CH2:15][C@:4]4([CH3:3])[O:8][C:7]5=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]5[CH2:5]4)[CH2:21][CH2:20]3)=[O:42])[CH2:37][CH:36]=2)=[CH:31][CH:30]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 230816374-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchlorideHCID 69481767(S)-2-methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride

생성물 1

HCID 69479749(S)-[4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]methanone
수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A mixture of (S)-2-methyl-6-nitro-2-(piperazin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole dihydrochloride prepared in Example 408 (401 mg, 1.5 mmol), DMF (8 ml) and potassium carbonate (750 mg, 5.4 mmol) was stirred at room temperature for 10 minutes. To the reaction mixture, a solution of 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchloride (400 mg, 1.56 mmol) in DMF (3 ml) was added slowly with cooling on ice-bath followed by stirring at room temperature overnight. To the reaction mixture, water was added, and the solution was extracted with ethyl acetate. The organic phase was washed with water three times and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanol to afford (S)-[4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridin-1-yl]-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]methanone (380 mg, yield 53%) as a light yellow powder.

후처리

  1. temperaturewith cooling on ice-bath
  2. stirringby stirring at room temperature overnight
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic phase was washed with water three times
  5. dry with materiala saturated saline solution, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-2bbc24c329f74077b6aca330a70233e5
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262212B2

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