Triethylamine → HCID 117798604, compound

HRID 1497388Notes

Reaction equation

HRID 1497388 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([N:12]3[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][C:13]3=[O:20])=[CH:8]2)=[N:3]1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[CH3:28][S:29]([O:19][CH2:18][C:15]1[CH:16]=[CH:17][N:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[C:10]([CH3:11])[N:2]([CH3:1])[N:3]=3)[CH:8]=2)[C:13](=[O:20])[CH:14]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117798896HCID 117798896, compound

Product 1

HCID 117798604HCID 117798604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2,3-dimethyl-2H-indazol-5-yl)-4-(hydroxymethyl)pyridin-2(1H)-one (100 mg) in dichloromethane (5 ml) was added triethylamine (0.153 ml) at 0° C., and the mixture was stirred at the same temperature for 30 min. To the obtained reaction mixture was added methanesulfonyl chloride (0.057 ml) at 0° C., and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (120 mg).

Workup

  1. customTo the obtained reaction mixture
  2. stirringthe mixture was stirred at room temperature for 4 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with dichloromethane
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-06d5763a4afa457b8bc3a6a84f6d93b0
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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