Dimethyl Sulfoxide → HCID 67098566, compound

HRID 2077088Notes

Reaction equation

HRID 2077088 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.[CH3:19][C:20]1[N:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][NH2:29])=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+].CS(C)=O>O>[CH3:19][C:20]1[N:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][NH:29][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 119835452-chloro-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrileHCID 67097542HCID 67097542, compound

Product 1

HCID 67098566HCID 67098566, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound A (300 mg, 1.22 mmol), 2-(6-methylpyridin-3-yloxy)ethylamine hydrochloride (549 mg) and sodium hydrogencarbonate (1.02 g) were added to DMSO (10 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-(6-methylpyridin-3-yloxy)ethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrile (88 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-153799f2bc3a47108e3dc38d10bc334a
Source dataset
uspto-grants-2011_04
Patent number
US07928126B2

Reaction notes

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