Hydrochloric Acid → HCID 57326798, compound

HRID 709262Notes

Reaction equation

HRID 709262 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-ec6a8350e4674bb6a20dd0198ed6e4f6
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

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