Methyl iodide → HCID 58968731, 화합물

HRID 2075088노트

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HRID 2075088 반응식
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([CH:28]1[CH2:31][CH2:30][CH2:29]1)([OH:27])[CH3:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[H-].[Na+].I[CH3:44]>O1CCCC1>[CH:28]1([C:25]([C:16]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][C:15]=2[CH2:14][N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:39])[F:40])[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=2)[C:8]2[N:9]=[N:10][N:11]([CH3:13])[N:12]=2)([O:27][CH3:44])[CH3:26])[CH2:31][CH2:30][CH2:29]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58968647HCID 58968647, 화합물

생성물 1

HCID 58968731HCID 58968731, 화합물수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(2-(((3,5-bis(trifluoromethyl)benzyl)(2-methyl-2H-tetrazol-5-yl)amino)methyl)-4-(trifluoromethyl)phenyl)-1-cyclobutylethanol (22 mg; 0.038 mmol) in tetrahydrofuran (1.5 mL) was added sodium hydride (10 mg; 0.25 mmol; 60% dispersion in mineral oil). The reaction was stirred for 10 minutes. Iodomethane (0.05 mL; 0.80 mmol) was added. The reaction was stirred at room temperature for 16 hours. The reaction was quenched with water. The mixture was diluted with ethyl acetate and filtered over sodium sulfate and silica get column. After being concentrated under reduced pressure, the residue was taken up in ethyl acetate and washed with water (2×) and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over a 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-50% ethyl acetate in hexanes) to give 18 mg (80% yield) of the title compound as a colorless gum. MS (ES+): Calc: 595.5, Found: 596.5 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.73 (s, 2H), 7.45 (d, J=8.3 Hz, 1H), 7.43 (s, 1H), 7.3 (d, J=8.3 Hz, 1H), 5.09 (s, 2H), 4.8 (q, J=16.18 Hz, 2H), 4.2 (s, 3H), 3.04 (s, 3H), 2.83 (m, 1H) 1.99 (m, 1H), 1.89-1.6 (m, 6H), 1.59 (s, 3H).

후처리

  1. stirringThe reaction was stirred at room temperature for 16 hours
  2. customThe reaction was quenched with water
  3. additionThe mixture was diluted with ethyl acetate
  4. filtrationfiltered over sodium sulfate and silica
  5. customget column
  6. concentrationAfter being concentrated under reduced pressure
  7. washwashed with water (2×) and brine
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified over a 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-3e364ffe696e4f88914c23dc5181b1ce
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919506B2

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