Hydrochloric Acid → HCID 57326798, compound

HRID 1183988Notes

Reaction equation

HRID 1183988 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-ddd23b4a956849b6b8d92183992aa0fd
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Reaction notes

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