Hydrochloric Acid → HCID 178448523, compound

HRID 1625037Notes

Reaction equation

HRID 1625037 reaction equation
Cl.[F:2][C:3]1[C:4]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C@H:36]3[CH2:41][CH2:40][C@H:39]([O:42]C4CCCCO4)[CH2:38][CH2:37]3)=[CH:30][CH:29]=2)=[CH:5][C:6](=[O:27])[N:7]([CH2:9][CH2:10][C@@:11]([CH3:26])([S:22]([CH3:25])(=[O:24])=[O:23])[C:12]([NH:14][O:15]C2CCCCO2)=[O:13])[CH:8]=1>O1CCOCC1.C(Cl)Cl.O>[F:2][C:3]1[C:4]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C@H:36]3[CH2:41][CH2:40][C@H:39]([OH:42])[CH2:38][CH2:37]3)=[CH:30][CH:29]=2)=[CH:5][C:6](=[O:27])[N:7]([CH2:9][CH2:10][C@@:11]([CH3:26])([S:22]([CH3:25])(=[O:23])=[O:24])[C:12]([NH:14][OH:15])=[O:13])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178448521HCID 178448521, compound

Product 1

HCID 178448523HCID 178448523, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 866687791,4 Dioxane dichloromethane waterSolvent

Procedure

Hydrochloric acid (4.0 M in 1, 4-dioxane, 1.7 mL, 6.63 mmol) was added to a solution of (2R)-4-[5-fluoro-2-oxo-4-(4-{[trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methoxy}phenyl)-pyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (450 mg, 0.66 mmol) in 1,4-dioxane:DCM:water (2:2:1, 5 mL) at room temperature. After 1 h, the reaction was concentrated under reduced pressure. The crude residue was triturated in ethanol (10 mL) overnight. The solid was collected via filtration, washed with ethanol (5 mL), and dried under reduced pressure to afford the title compound as a white solid (110 mg, 33%). MS (LCMS) m/z 511.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97-1.19 (m, 4 H) 1.54 (s, 3 H) 1.58-1.72 (m, 1 H) 1.72-1.89 (m, 4 H) 2.04-2.23 (m, 1 H) 2.41 (m, 1 H) 3.08 (s, 3 H) 3.18-3.40 (m, 1 H) 3.65-3.84 (m, 3 H) 4.01 (td, J=11.61, 4.88 Hz, 1 H) 4.49 (br. s., 1 H) 6.45 (d, J=7.81 Hz, 1 H) 6.94-7.06 (m, 2 H) 7.36-7.54 (m, 2 H) 7.96 (d, J=6.83 Hz, 1 H) 9.21 (s, 1 H) 11.07 (s, 1 H) 11.12 (s, 1 H).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customThe crude residue was triturated in ethanol (10 mL) overnight
  3. filtrationThe solid was collected via filtration
  4. washwashed with ethanol (5 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-af043d2e002b40fc903a7ceb6bae90c2
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

Loading…