Dimethyl Sulfoxide → HCID 67098443, compound

HRID 2077079Notes

Reaction equation

HRID 2077079 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][O:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[O:23][CH2:24][CH2:25][NH2:26].C(=O)([O-])O.[Na+].CS(C)=O>O>[CH3:19][O:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[O:23][CH2:24][CH2:25][NH:26][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]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 27627342-(2-Methoxyphenoxy)ethan-1-amine--hydrogen chloride (1/1)HCID 119835452-chloro-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrile

Product 1

HCID 67098443HCID 67098443, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound A (400 mg, 1.63 mmol), 2-(2-methoxyphenoxy)ethylamine hydrochloride (1.10 g) and sodium hydrogencarbonate (1.37 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-(2-methoxyphenoxy)ethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrile (89 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-e5343d693c0844469a32ddfebbfa8571
Source dataset
uspto-grants-2011_04
Patent number
US07928126B2

Reaction notes

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