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

HRID 335088Notes

Reaction equation

HRID 335088 reaction equation
[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

Participants

6

Reactant 3

HCID 15303P-Toluenesulfonylhydrazide2×HCID 517045Sodium AcetateHCID 247659313-(Cyclohex-2-enyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-327c676a738b4bbda288bcb0ba96dc49
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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