Water → HCID 57736462, compound

HRID 1641756Notes

Reaction equation

HRID 1641756 reaction equation
[OH:1][CH:2]([C:13]1[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=1[F:21])[C:3]1[C:4]([CH3:12])=[CH:5][C:6]([C:9]([NH2:11])=[O:10])=[N:7][CH:8]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(N(CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[CH3:22][S:23]([O:1][CH:2]([C:3]1[CH:8]=[N:7][C:6]([C:9](=[O:10])[NH2:11])=[CH:5][C:4]=1[CH3:12])[C:13]1[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=1[F:21])(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57736499HCID 57736499, compound

Product 1

HCID 57736462HCID 57736462, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[hydroxy(2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide (7.11 g, 24.0 mmol) in N,N-dimethylformamide (150 ml), methanesulfonyl chloride (3.72 ml, 48.0 mmol) and then triethylamine (13.4 ml, 96.0 mmol) were added in a nitrogen atmosphere at 0° C., and the mixture was stirred for 2 hours at room temperature. Water and ethyl acetate were added to the reaction mixture at 0° C., the organic layer was separated, and the organic layer was washed sequentially with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography, and the fraction obtained from an elution with dichloromethane:methanol=49:1 was concentrated under reduced pressure, to obtain the title compound (4.71 g, 12.6 mmol, 52%) as a pale brown foamy substance.

Workup

  1. customthe organic layer was separated
  2. washthe organic layer was washed sequentially with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe fraction obtained from an elution with dichloromethane
  7. concentrationmethanol=49:1 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f999a02a5024450db723aa39944c4791
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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