Hydrochloric Acid → HCID 86671938, compound

HRID 84252Notes

Reaction equation

HRID 84252 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%). 1H NMR (400 MHz, CD3OD, δ ppm 1.72 (s, 3H), 1.83-1.91 (m, 2H), 2.41 (ddd, J=13.4, 10.9, 5.4 Hz, 1H), 2.66 (ddd, J=13.6, 10.8, 5.4 Hz, 1H), 2.76 (m, 2H), 3.10 (s, 3H), 3.59 (t, J=6.4 Hz, 2H), 4.05 (ddd, J=12.5, 10.5, 5.2 Hz, 1H), 4.38 (ddd, J=12.9, 10.7, 5.0 Hz, 1H), 6.95 (d, J=1.8 Hz, 1H), 7.00 (m, 1H), 7.38 (br d, J=8.3 Hz, 2H), 7.66 (br d, J=8.3 Hz, 2H), 7.87 (d, J=7.1 Hz, 1H). LCMS: 423.3 (M+1).

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-af6dfb044a8e4d0d9afea7a182792cd9
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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