Ammonium Chloride → N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 361453노트

반응식

HRID 361453 반응식
C(OCC(C)OCC1C=CC([C:16]2[C:21]([S:22]([NH:25][C:26]3[C:31]([O:32][CH3:33])=[N:30][C:29]([CH3:34])=[CH:28][N:27]=3)(=[O:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=2)=CC=1)(C)(C)C.[Cl-].[NH4+]>FC(F)(F)C(O)=O>[CH3:33][O:32][C:31]1[C:26]([NH:25][S:22]([C:21]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:23])=[O:24])=[N:27][CH:28]=[C:29]([CH3:34])[N:30]=1

참가 물질

4

반응물 2

HCID 25517Ammonium ChlorideHCID 211862852-{4-[(2-tert-butoxy-1-methylethoxy)methyl]phenyl}-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

생성물 1

HCID 23226620N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide수율 59.1%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of 2-{4-[(2-tert-butoxy-1-methylethoxy)methyl]phenyl}-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (248 mg) in trifluoroacetic acid (1 ml) was left to stand for 30 minutes. Saturated ammonium chloride solution (20 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml). The extracts were dried (MgSO4) and concentrated and the residue was dissolved in dichloromethane (10 ml). The solution was washed with water (2×10 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with methanol/ethyl acetate (1:24 v/v), to give 2-[4-([2-hydroxy-1-methyl)ethoxy]methyl) phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (82 mg), 1H NMR (d6 -DMSO): 1.15 (s, 3 H), 2.25 (s, 3 H), 3.3-3.7 (s, 3 H), 3.8 (s, 3 H), 4.6 (s, 2 H), 7.3-7.55 (m, 5 H), 7.6 (dd, 1 H), 8.45 (dd, 1 H), 8.8 (dd, 1 H), 10.35-10.45 (br s, 1 H); mass spectrum (+ve ESP): 445 (M+H)+.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  2. dry with materialThe extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in dichloromethane (10 ml)
  5. washThe solution was washed with water (2×10 ml)
  6. dry with materialdried (MgSO4)
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified by flash chromatography
  9. washeluting with methanol/ethyl acetate (1:24 v/v)

출처 및 근거

ORD 기록
ord-6d304c80d07743adb463ae74fd577962
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866568

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