Dimethyl Sulfoxide → HCID 67098421, compound

HRID 2077082Notes

Reaction equation

HRID 2077082 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].[N:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][NH2:27])=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+].CS(C)=O>O>[N:18]1[CH:23]=[CH:22][C:21]([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:20][CH:19]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 119835452-chloro-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrileHCID 121366312-(Pyridin-4-yloxy)ethanamine

Product 1

HCID 67098421HCID 67098421, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound A (400 mg, 1.63 mmol), 2-(pyridin-4-yloxy)ethylamine (540 μl) and sodium hydrogencarbonate (1.32 g) were added to DMSO (12 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-(pyridin-4-yloxy)ethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrile (23 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-70829832bf0c47b8824807b48a37dfec
Source dataset
uspto-grants-2011_04
Patent number
US07928126B2

Reaction notes

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