Hydrochloric Acid → HCID 86671936, compound

HRID 84251Notes

Reaction equation

HRID 84251 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]([CH2:18][CH2:19][C:20]([CH3:35])([S:31]([CH3:34])(=[O:33])=[O:32])[C:21]([NH:23][O:24]C3CCCCO3)=[O:22])[C:14](=[O:36])[CH:13]=2)=[CH:8][CH:7]=1.Cl>O1CCOCC1.CO>[OH:24][NH:23][C:21](=[O:22])[C:20]([CH3:35])([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:19][CH2:18][N:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:7][CH:8]=2)=[CH:13][C:14]1=[O:36]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86671935HCID 86671935, compound

Product 1

HCID 86671936HCID 86671936, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To 4-(4-(4-(3-hydroxypropoxy)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (120 mg, 0.230 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 in vacuo onto silica gel. Chromatography on silica gel with a dichloromethane-methanol gradient (1%-25%) gave the title compound as a white foam (20.8 mg, 20.1%). 1H NMR: 400 MHz, (CD3OD) δ ppm 1.71 (s, 3H), 2.06 (m, 2H), 2.38 (ddd, J=13.2, 10.8, 4.8 Hz, 1H), 2.53-2.62 (m, 1H), 3.11 (s, 3H), 3.76 (t, J=6.2 Hz, 2H), 3.88-3.96 (m, 1H), 4.14 (t, J=6.3 Hz, 2H), 4.29 (ddd, J=12.5, 10.8, 4.9 Hz, 1H), 6.75 (m, 2H), 7.04 (d, J=8.7 Hz, 2H), 7.62-7.69 (m, 3H). LCMS: 437.2 (M−1).

Workup

  1. customevaporated in vacuo onto silica gel

Sources & evidence

ORD record
ord-4ac503010c5c47e2bdd552d3085d7e0b
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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