Dimethylformamide → (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid N-methyl-N-(4-trifluoromethylphenyl)amide

HRID 856331노트

반응식

HRID 856331 반응식
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@:19]3([CH3:30])[O:23][C:22]4=[N:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][N:21]4[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])=[CH:5][CH:4]=1.[CH3:33]N(C=O)C.[H-].[Na+].CI>O>[CH3:33][N:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:31])[F:32])=[CH:8][CH:7]=1)[C:10]([N:12]1[CH2:13][CH2:14][N:15]([CH2:18][C@:19]2([CH3:30])[O:23][C:22]3=[N:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][N:21]3[CH2:20]2)[CH2:16][CH2:17]1)=[O:11]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86604818(S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid (4-trifluoromethylphenyl)amide

생성물 1

HCID 69482847(S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid N-methyl-N-(4-trifluoromethylphenyl)amide수율 17%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylic acid (4-trifluoromethylphenyl)amide prepared in Example 477 (200 mg, 0.44 mmol), DMF (4 ml), and sodium hydride (26 mg, 0.66 mmol) was stirred at room temperature for 1.5 hours. To the mixture, methyl iodide (0.5 ml, 0.76 mmol) was added followed by stirring at room temperature overnight. To the reaction mixture, water was added, and the mixture 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 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)piperazine-1-carboxylic acid N-methyl-N-(4-trifluoromethylphenyl)amide (35 mg, yield 17%) as a white powder.

후처리

  1. stirringby stirring at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water three 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 (methylene chloride/methanol=50/1)

출처 및 근거

ORD 기록
ord-aa6c8408f2ac4dda8843a2c162afe26b
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

반응 노트

불러오는 중…