P-Toluenesulfonylhydrazide → HCID 59225698, compound

HRID 1426145Notes

Reaction equation

HRID 1426145 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:22]=[CH:23]/[C:24]([O:26][CH3:27])=[O:25])[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(NN)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 16661153HCID 16661153, compound

Product 1

HCID 59225698HCID 59225698, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 25 mL round-bottomed flask was charged with (E)-methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)acrylate (430 mg, 1.13 mmol), 4-methylbenzenesulfonohydrazide (1050 mg, 5.64 mmol) and toluene (10 mL). The reaction was heated to reflux for 12 hours. The reaction was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (20% EtOAc in hexanes) to afford the title compound (140 mg, 32.4% yield) as a white solid. 1H NMR (CDCl3) δ 8.49 (s, 1H), 7.80 (d, 1H), 7.41 (m, 5H), 7.00 (d, 1H), 6.37 (q, 1H), 5.08 (s, 2H), 3.67 (s, 3H), 2.89 (t, 2H), 2.61 (t, 2H), 2.31 (d, 3H). Mass spectrum (apci) m/z=384.1 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 12 hours
  3. customThe reaction was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5fecec270d264a38b54bdeb171228fc1
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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