Dimethyl Sulfoxide → HCID 67098970, compound

HRID 2077091Notes

Reaction equation

HRID 2077091 reaction equation
[Cl:1][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:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[O:21][CH2:22][CH2:23][NH2:24].C(=O)([O-])O.[Na+].CS(C)=O>O>[ClH:1].[Cl:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[O:21][CH2:22][CH2:23][NH:24][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 27357882-(2-Chlorophenoxy)EthylamineHCID 119835452-chloro-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrile

Product 1

HCID 67098970HCID 67098970, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Compound A (200 mg, 813 μmol), 2-(2-chlorophenoxy)ethylamine (280 μl) 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. This was converted to hydrochloride to give the object compound of 2-(2-(2-chlorophenoxy)ethylamino)-6-(5-methyl-1H-pyrazol-3-ylamino)-4-methylnicotinonitrile hydrochloride (18 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-ebbdc95c02e143f894b3d149257e4733
Source dataset
uspto-grants-2011_04
Patent number
US07928126B2

Reaction notes

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