P-Toluenesulfonylhydrazide → Methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)propanoate

HRID 911784Notes

Reaction equation

HRID 911784 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17])=[CH:10][C:9]=2[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:5][CH:6]=1.CC1C=CC(S(NN)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:10][C:9]=2[O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 86631473(E)-methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)acrylate

Product 1

HCID 24764521Methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)propanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of mL (E)-methyl 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-yl)acrylate (500 mg, 1.36 mmol), 4-methylbenzenesulfonohydrazide (1.27 g, 6.8 mmol), and toluene (15 mL) was heated at reflux for 12 hours, cooled to room temperature and concentrated. The residue was purified by silica gel (20 to 30% EtOAc in hexanes) to afford the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel (20 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1717651b11164dc98f36c8ed211de614
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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