P-Toluenesulfonylhydrazide → HCID 57898922, compound

HRID 911026Notes

Reaction equation

HRID 911026 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[O:4][C:5]1[CH:10]=[C:9]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH3:17])[N:16]=2)[N:8]=[CH:7][C:6]=1/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21].CC1C=CC(S(NN)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[O:4][C:5]1[CH:10]=[C:9]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH3:17])[N:16]=2)[N:8]=[CH:7][C:6]=1[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 86634752HCID 86634752, compound

Product 1

HCID 57898922HCID 57898922, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 25 mL round-bottomed flask is charged with (E)-methyl 3-(4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)acrylate (455 mg, 1.13 mmol), 4-methylbenzenesulfonohydrazide (1050 mg, 5.64 mmol), and toluene (10 mL). The reaction mixture is heated at reflux for 12 hours, then cooled to room temperature and concentrated in vacuo. The residue is purified by silica gel (20 to 30% EtOAc in hexanes) to afford methyl 3-(4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)propanoate.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 12 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel (20 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0383175c202c4a5fbc5976264938025d
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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