Methylhydrazine → 1-[4-[4-[5-(2,6-Difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-(1-methylhydrazinyl)ethanone

HRID 1916444Notes

Reaction equation

HRID 1916444 reaction equation
[CH3:1][NH:2][NH2:3].Cl[CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH2:23][CH:22]([C:24]4[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=4[F:31])[O:21][N:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7]>O1CCCC1>[F:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([F:30])[C:24]=1[CH:22]1[O:21][N:20]=[C:19]([C:17]2[N:18]=[C:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6](=[O:7])[CH2:5][N:2]([CH3:1])[NH2:3])[CH2:13][CH2:12]3)[S:15][CH:16]=2)[CH2:23]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 673742792-Chloro-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone

Product 1

HCID 673749051-[4-[4-[5-(2,6-Difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-(1-methylhydrazinyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of methyl hydrazine (532 μL, 10.0 mmol) in tetrahydrofuran (1 mL) at 0° C. was added dropwise a solution of 2-chloro-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone (i.e. the product of Example 2, Step A) (425 mg, 1.0 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred at room temperature overnight, and then concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane, washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as an oil (0.59 g weight including residual tetrahydrofuran), which was used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in dichloromethane
  3. washwashed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b84d7f90a2d64bf294879dc0b20794e3
Source dataset
uspto-grants-2013_12
Patent number
US08618137B2

Reaction notes

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