Hydrochloric Acid → HCID 57326798, compound

HRID 84280Notes

Reaction equation

HRID 84280 reaction equation
Cl.[CH:2]1([C:8]2[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][C:16]([CH3:31])([S:27]([CH3:30])(=[O:29])=[O:28])[C:17]([NH:19][O:20]C3CCCCO3)=[O:18])[C:10](=[O:32])[CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CO>O1CCOCC1.ClCCl>[CH:2]1([C:8]2[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][C:16]([CH3:31])([S:27]([CH3:30])(=[O:29])=[O:28])[C:17]([NH:19][OH:20])=[O:18])[C:10](=[O:32])[CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 866719534-(4-cyclohexyl-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 57326798HCID 57326798, compoundYield 202.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4.0 M solution of HCl in 1,4-dioxane (3.3 mL) was added slowly to a solution of the 4-(4-cyclohexyl-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (220 mg, 0.14 mmol) in dichloromethane (5 mL) followed by methanol (1 mL) at room temperature. The reaction was concentrated in vacuo and the title compound was purified using reverse phase chromatography (Gradient used with formic acid modifier(0.05%), 95:5 water:acetonitrile to 5:95 water:acetonitrile). Gradient time 6 minutes. Furnished a white solid (105 mg, 58.6%) MS (LC/MS) m/z 371.6 (M+1)

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe title compound was purified
  3. customGradient time 6 minutes

Sources & evidence

ORD record
ord-933b3221ad8843f49b9d3c38994921c3
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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