Sodium Carbonate → HCID 86631244, compound

HRID 1023031Notes

Reaction equation

HRID 1023031 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16](=[S:18])[NH2:17])[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[CH:3]=1.Cl[CH2:24][C:25]([CH2:27]Cl)=O.C(=O)([O-])[O-:30].[Na+].[Na+]>C(O)(C)C.O>[CH:24]([C:25]1[N:17]=[C:16]([CH:13]2[CH2:14][CH2:15][N:10]([C:8](=[O:9])[CH2:7][N:6]3[C:2]([CH3:1])=[CH:3][C:4]([C:19]([F:22])([F:20])[F:21])=[N:5]3)[CH2:11][CH2:12]2)[S:18][CH:27]=1)=[O:30]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 107931,3-DichloroacetoneHCID 580788971-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinecarbothioamide2×

Product 1

HCID 86631244HCID 86631244, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

To a mixture of 1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinecarbothioamide (i.e. the product of Example 1, Step C) (20 g, 59.9 mmol) in isopropyl alcohol (90 mL) was added 1,3-dichloroacetone (8.99 g, 71.3 mmol) and the reaction mixture heated at 65 for 1.5 h. After cooling, a solution of sodium carbonate (7.39 g, 70.0 mmol) in water (92 mL) was added dropwise. After 2 h additional water (31 mL) was added and the resulting precipitate rinsed with water (62 mL). Drying overnight under reduced pressure at 45° C. provided 18.24 g of the title compound as a light gray solid.

Workup

  1. temperaturethe reaction mixture heated at 65 for 1.5 h
  2. temperatureAfter cooling
  3. washthe resulting precipitate rinsed with water (62 mL)
  4. customDrying overnight under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-dad09026260541d0811df6c11509636e
Source dataset
uspto-grants-2014_05
Patent number
US08722678B2

Reaction notes

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