Triethylamine → N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide

HRID 595691노트

반응식

HRID 595691 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O[Li].O>C(Cl)Cl.CCOC(C)=O.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH:15][S:24]([CH3:23])(=[O:26])=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 288900524-(Benzyloxy)pyridin-3-amine

생성물 1

HCID 59233662N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide수율 54%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-(benzyloxy)pyridin-3-amine (40 g, 0.2 mol) and Et3N (60.6 g, 0.6 mol) in DCM (600 mL), MsCl (45.8 g, 0.4 mol) was added dropwise at 0° C. The mixture was allowed to warm up to room temperature and stirred overnight. The reaction mixture was quenched with NaHCO3 and extracted with DCM. The organic phase was washed with brine, dried over Na2SO4, and concentrated. The residue was dissolved in THF:H2O=5:1 (500 mL) and LiOH.H2O (16.8 g, 0.4 mmol) was added. The mixture was stirred for 4 hours at room temperature. EtOAc (300 mL) was added, and the organic phase washed with NaHCO3 (sat., a.q.), brine, dried over Na2SO4, filtrated and concentrated to give pure N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide (30.0 g, yield: 54.0%). 1H-NMR (CDCl3, 400 MHz) δ 8.67 (s, 1H), 8.34 (d, J=5.6 Hz, 1H), 7.35˜7.42 (m, 5H), 6.91 (d, J=5.6 Hz, 1H), 6.61 (br, 1H), 5.15 (s, 2H), 2.96 (s, 3H). MS (M+H)+: 279.

후처리

  1. customThe reaction mixture was quenched with NaHCO3
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in THF
  7. stirringThe mixture was stirred for 4 hours at room temperature
  8. washthe organic phase washed with NaHCO3 (sat., a.q.), brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltrated
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cc2cd0b0de67426a9ba7918ac4d946af
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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