4-Methylmorpholine → N-{6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl}methanesulphonamide

HRID 2359916Notes

Reaction equation

HRID 2359916 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([NH2:18])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1.CN1CCOCC1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([NH:18][S:27]([CH3:26])(=[O:29])=[O:28])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 583368116-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-amine

Product 1

HCID 66634052N-{6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl}methanesulphonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

146 mg (585 μmol) of 6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-amine and 54.0 μl (701 μmol) of N-methylmorpholine were initially charged in 10 ml of dichloromethane, and methanesulphonyl chloride was added at room temperature. The mixture was stirred overnight and the reaction mixture was filtered through silica gel (eluent: ethyl acetate). After concentration, the crude product was purified by chromatography (dichloromethane/methanol).

Workup

  1. filtrationthe reaction mixture was filtered through silica gel (eluent: ethyl acetate)
  2. concentrationAfter concentration
  3. customthe crude product was purified by chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-6bd5b3f24ea641ec97119f49994a54b6
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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