Water → HCID 71270957, compound

HRID 510447Notes

Reaction equation

HRID 510447 reaction equation
[CH3:1][C:2]1[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[C:22]=2[CH3:31])=[C:5]2[N:6]=[C:7]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:8]=[C:9]([C:10]([NH2:12])=O)[N:4]2[N:3]=1.S(Cl)(Cl)=O.O>CN(C)C=O>[CH3:1][C:2]1[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[C:22]=2[CH3:31])=[C:5]2[N:6]=[C:7]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:8]=[C:9]([C:10]#[N:12])[N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 71270913HCID 71270913, compound

Product 1

HCID 71270957HCID 71270957, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-5-(4-morpholinyl)pyrazolo[1,5-a]pyrimidine-7-carboxamide (200 mg, 0.461 mmol) in N,N-Dimethylformamide (DMF) (6 mL) was added thionyl chloride (0.067 mL, 0.923 mmol). The reaction mixture was stirred at rt for 2 h. Water was added in. The solid precipitated. Filtration gave the crude product. The crude was purified on silica column (20˜50% EtOAc/Hexane) to give the titled product (0.14 g, 77%). MS (ES+) m/e 416.2 [M+H]+.

Workup

  1. customThe solid precipitated
  2. filtrationFiltration
  3. customgave the crude product
  4. customThe crude was purified on silica column (20˜50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-ce40689ad3df4371b56ecea9731b8249
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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