P-Toluenesulfonylhydrazide → 3-(cyclohexyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

HRID 335088노트

반응식

HRID 335088 반응식
[CH:1]1([O:7][C:8]2[C:9]([NH:14][C:15]3[S:16][CH:17]=[C:18]([CH3:20])[N:19]=3)=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.CC1C=CC(S(NN)(=O)=O)=CC=1.CC([O-])=O.[Na+]>C(COC)OC.O>[CH:1]1([O:7][C:8]2[C:9]([NH:14][C:15]3[S:16][CH:17]=[C:18]([CH3:20])[N:19]=3)=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

6

반응물 3

HCID 15303P-Toluenesulfonylhydrazide2회HCID 517045Sodium AcetateHCID 247659313-(Cyclohex-2-enyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

생성물 1

HCID 247659333-(cyclohexyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine수율 55.3%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

3-(Cyclohex-2-enyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.115 g, 0.400 mmol) and 4-methylbenzenesulfonohydrazide (1.12 g, 6.00 mmol) were placed in dimethoxyethane (5 mL). NaOAc (0.492 g, 6.00 mmol) was dissolved in water (2 mL) and added to the above solution and refluxed. Additional 4-methylbenzenesulfonohydrazide (1.12 g, 6.00 mmol) was added and the reaction mixture was refluxed overnight. An aqueous work up was done and the crude material was purified by silica gel chromatography to provide 3-(cyclohexyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.064 g, 55.3%) after HCl salt formation. 1H NMR (d6-DMSO) δ 7.79 (d, 1H), 7.57 (d, 1H), 7.09 (m, 1H), 6.83 (s, 1H), 4.54 (m, 1H), 2.32 (s, 3H), 1.97 (m, 2H), 1.79, (m, 2H), 1.57 (m, 3H), 1.36 (m, 3H); Mass spectrum (apci) m/z=291.1 (M+H—HCl).

후처리

  1. additionadded to the above solution
  2. temperaturerefluxed
  3. temperaturethe reaction mixture was refluxed overnight
  4. customthe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-327c676a738b4bbda288bcb0ba96dc49
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883828B2

반응 노트

불러오는 중…