Hydrochloric Acid → HCID 86671938, compound

HRID 1475844Notes

Reaction equation

HRID 1475844 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][C:19]([CH3:34])([S:30]([CH3:33])(=[O:32])=[O:31])[C:20]([NH:22][O:23]C3CCCCO3)=[O:21])[C:13](=[O:35])[CH:12]=2)=[CH:7][CH:6]=1.Cl>O1CCOCC1.CO>[OH:23][NH:22][C:20](=[O:21])[C:19]([CH3:34])([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:18][CH2:17][N:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=2)=[CH:12][C:13]1=[O:35]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86671937HCID 86671937, compound

Product 1

HCID 86671938HCID 86671938, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To 4-{4-[4-(3-hydroxypropyl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (213 mg, 0.420 mmol) was added 4 N hydrogen chloride in dioxane (5.0 mL) and methanol (0.50 mL). The reaction was stirred for 30 minutes and then evaporated to dryness. The residue was dissolved in minimal dichloromethane (2.0 mL) and diluted with ether to produce a precipitate. The suspension was stirred overnight at room temperature. The resulting solid was allowed to settle and the liquid was decanted off. The solid was rinsed twice with ether and dried on a vacuum pump to give the title compound as a white solid (164 mg, 92.4%).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in minimal dichloromethane (2.0 mL)
  3. additiondiluted with ether
  4. customto produce a precipitate
  5. stirringThe suspension was stirred overnight at room temperature
  6. customthe liquid was decanted off
  7. washThe solid was rinsed twice with ether
  8. customdried on a vacuum pump

Sources & evidence

ORD record
ord-86f5ad8cca6b445aa7d07b71c9028741
Source dataset
uspto-grants-2015_04
Patent number
US09018384B2

Reaction notes

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