Hydrochloric Acid → HCID 178448465, compound

HRID 709206Notes

Reaction equation

HRID 709206 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 178448463HCID 178448463, compound

Product 1

HCID 178448465HCID 178448465, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (1.0 N in water, 2.17 mL) was added to a solution of (2R)-4-{4-[4-(trans-3-hydroxycyclobutyl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (375 mg, 0.723 mmol) in 1,4-dioxane (5 mL). After 1 hour, the reaction was concentrated to give a brown solid. The solid was triturated with 2-propanol at 50° C., for 30 minutes. After cooling, filtration afforded the title compound as a white solid (187 mg, 60%). LCMS m/z 435.6 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3H) 2.11-2.23 (m, 1H) 2.26-2.38 (m, 4H) 2.38-2.48 (m, 1H) 3.11 (s, 3H) 3.42-3.60 (m, 1H) 3.74 (td, J=12.00, 4.68 Hz, 1H) 4.00-4.21 (m, 1H) 4.25-4.42 (m, 1H) 6.58-6.72 (m, 2H) 7.36 (d, J=8.20 Hz, 2H) 7.61-7.71 (m, 2H) 7.74 (d, J=7.22 Hz, 1H) 11.17 (br. s., 1H)

Workup

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

Sources & evidence

ORD record
ord-1c3dd1678f4b451eb5369cc23e711e33
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

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