Hydrochloric Acid → HCID 86671912, compound

HRID 84222Notes

Reaction equation

HRID 84222 reaction equation
[ClH:1].[F:2][C:3]1([F:44])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][N:22]([CH2:25][CH2:26][C:27]([CH3:42])([S:38]([CH3:41])(=[O:40])=[O:39])[C:28]([NH:30][O:31]C4CCCCO4)=[O:29])[C:21](=[O:43])[CH:20]=3)=[CH:15][CH:14]=2)[CH2:5][CH2:4]1>O1CCOCC1.O>[ClH:1].[F:44][C:3]1([F:2])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][N:22]([CH2:25][CH2:26][C:27]([CH3:42])([S:38]([CH3:41])(=[O:39])=[O:40])[C:28]([NH:30][OH:31])=[O:29])[C:21](=[O:43])[CH:20]=3)=[CH:17][CH:18]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86671914HCID 86671914, compound

Product 1

HCID 86671912HCID 86671912, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

HCl (4.0 M in 1,4-dioxane, 1.0 mL) was added to a solution of 4-[4-{4-[3-(4,4-difluoropiperidin-1-yl)propoxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (209 mg, 0.334 mmol) in 1,4-dioxane/water (1:1, 5 mL). After 10 minutes the reaction was concentrated to give a white solid, the solid was triturated with 2-propanol at 50° C. for 1 h. The title compound was isolated by filtration as a white solid (146 mg, the hydrochloride salt, 75%). LCMS m/z 542.8 (M+1) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3 H) 2.22 (br. s., 3 H) 2.38 (br. s., 5 H) 3.11 (s, 3 H) 3.13-3.26 (m, 2 H) 3.31 (br. s., 2 H) 3.74 (br. s., 3 H) 4.14 (t, J=5.76 Hz, 3 H) 6.59-6.72 (m, 2 H) 7.05 (d, J=8.78 Hz, 2 H) 7.63-7.79 (m, 3 H) 11.03 (br. s., 1 H) 11.18 (br. s., 1 H)

Workup

  1. concentrationAfter 10 minutes the reaction was concentrated
  2. customto give a white solid
  3. customthe solid was triturated with 2-propanol at 50° C. for 1 h

Sources & evidence

ORD record
ord-0df6d37212094bf9a000ecd75dc45837
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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