Hydrochloric Acid → HCID 178448464, compound

HRID 84223Notes

Reaction equation

HRID 84223 reaction equation
Cl.[OH:2][C@@H:3]1[CH2:6][C@H:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][N:16]([CH2:19][CH2:20][C@@:21]([CH3:36])([S:32]([CH3:35])(=[O:34])=[O:33])[C:22]([NH:24][O:25]C4CCCCO4)=[O:23])[C:15](=[O:37])[CH:14]=3)=[CH:9][CH:8]=2)[CH2:4]1>O1CCOCC1>[OH:25][NH:24][C:22](=[O:23])[C@:21]([CH3:36])([S:32]([CH3:35])(=[O:34])=[O:33])[CH2:20][CH2:19][N:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C@H:5]3[CH2:4][C@@H:3]([OH:2])[CH2:6]3)=[CH:8][CH:9]=2)=[CH:14][C:15]1=[O:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178448462HCID 178448462, compound

Product 1

HCID 178448464HCID 178448464, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (1.0 N in water, 3.58 mL) was added to a solution of (2R)-4-{4-[4-(cis-3-hydroxycyclobutyl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (620 mg, 1.20 mmol) in 1,4-dioxane (10 mL). After 2 hours the reaction was concentrated to give a brown solid. The solid was triturated with ethanol at 50° C., for 30 minutes. After cooling, filtration afforded the title compound as a white solid (384 mg, 74%). LCMS m/z 435.6 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (s, 3 H) 1.83-1.98 (m, 2 H) 2.11-2.24 (m, 1 H) 2.44 (d, J=17.95 Hz, 1 H) 2.54-2.69 (m, 2 H) 2.83-3.00 (m, 1 H) 3.11 (s, 3 H) 3.65-3.84 (m, 1 H) 3.98-4.18 (m, 2 H) 6.65 (dd, J=7.02, 2.15 Hz, 1 H) 6.69 (d, J=1.95 Hz, 1 H) 7.34 (d, J=8.20 Hz, 2 H) 7.62-7.71 (m, 2 H) 7.74 (d, J=7.02 Hz, 1 H) 11.17 (br. s., 1 H)

Workup

  1. concentrationAfter 2 hours the reaction was concentrated
  2. customto give a brown solid
  3. customThe solid was triturated with ethanol at 50° C., for 30 minutes
  4. temperatureAfter cooling
  5. filtrationfiltration

Sources & evidence

ORD record
ord-e20e4d6bd4d649ea80f13eac37007c9f
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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