Dimethyl Sulfoxide → HCID 67098657, compound

HRID 2077075Notes

Reaction equation

HRID 2077075 reaction equation
Cl[C:2]1[N:9]=[C:8]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)[CH:7]=[C:6]([C:17]([F:20])([F:19])[F:18])[C:3]=1[C:4]#[N:5].[O:21]([CH2:28][CH2:29][NH2:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+].CS(C)=O>O>[O:21]([CH2:28][CH2:29][NH:30][C:2]1[N:9]=[C:8]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)[CH:7]=[C:6]([C:17]([F:20])([F:19])[F:18])[C:3]=1[C:4]#[N:5])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 156512-PhenoxyethanamineHCID 516892Sodium BicarbonateHCID 11983550HCID 11983550, compound

Product 1

HCID 67098657HCID 67098657, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound F (300 mg, 1.00 mmol), 2-phenoxyethylamine (261 μl) and sodium hydrogencarbonate (837 mg) were added to DMSO (10 ml), and the mixture was stirred at 100° C. for 27 hr. After stirring, the reaction system was added to cold water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and concentrated, and the residue was washed by suspending in ethyl acetate to give the object compound of 2-(2-phenoxyethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-trifluoromethylnicotinonitrile (80 mg).

Workup

  1. stirringAfter stirring
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated
  5. washthe residue was washed

Sources & evidence

ORD record
ord-03b8f27eeb994b5e826ec43726566399
Source dataset
uspto-grants-2011_04
Patent number
US07928126B2

Reaction notes

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