Hydrochloric Acid → HCID 58380621, compound

HRID 1802880Notes

Reaction equation

HRID 1802880 reaction equation
CON(C)[C:4](=[O:21])[CH:5]([C:13]1[CH:17]=[C:16]([S:18][CH3:19])[N:15]([CH3:20])[N:14]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH:23]([Mg]Br)=[CH2:24].Cl>O1CCCC1>[CH3:20][N:15]1[C:16]([S:18][CH3:19])=[CH:17][C:13]([CH:5]([CH2:6][CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[C:4](=[O:21])[CH:23]=[CH2:24])=[N:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58380601N-methoxy-N-methyl-2-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamideHCID 178418507HCID 178418507, compound

Product 1

HCID 58380621HCID 58380621, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methyl-2-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide (0.80 g) in tetrahydrofuran (30 mL) was slowly added vinylmagnesium bromide (1.0M tetrahydrofuran solution: 7.3 ml) at room temperature under a nitrogen atmosphere, and the mixture was stirred for 30 min. The reaction mixture was poured into an ice-cooled 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (0.60 g, yield 83%) as a colorless oil from the fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 295 (MH+).

Workup

  1. customat room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-111a8ffbd228497bb90a505890438701
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Reaction notes

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