Dimethyl Sulfoxide → HCID 67097502, compound

HRID 2077081Notes

Reaction equation

HRID 2077081 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]([CH3:17])[C:3]=1[C:4]#[N:5].Cl.[F:19][C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][NH2:27])=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+].CS(C)=O>O>[F:19][C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][NH:27][C:2]2[N:9]=[C:8]([NH:10][C:11]3[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=3)[CH:7]=[C:6]([CH3:17])[C:3]=2[C:4]#[N:5])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 11983545HCID 11983545, compoundHCID 22061356Ethanamine, 2-(4-fluorophenoxy)-, hydrochloride (1:1)

Product 1

HCID 67097502HCID 67097502, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound A (200 mg, 813 mmol), 2-(4-fluorophenoxy)ethylamine hydrochloride (466 mg) and sodium hydrogencarbonate (683 mg) were added to DMSO (6 ml), and the mixture was stirred at 100° C. for 27 hr. After stirring, the reaction mixture 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-(4-fluorophenoxy)ethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrile (38 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-5520bf7e97f147e0a90cfa05412c23bf
Source dataset
uspto-grants-2011_04
Patent number
US07928126B2

Reaction notes

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