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

HRID 361453ノート

反応式

HRID 361453 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-6d304c80d07743adb463ae74fd577962
出典データセット
uspto-grants-1999_02
特許番号
US05866568

反応ノート

読み込み中…