Hydrochloric Acid → (2R)-N-hydroxy-4-[4-{4-[(6-methoxypyridin-3-yl)methoxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanamide

HRID 84303Notes

Reaction equation

HRID 84303 reaction equation
Cl.[CH3:2][O:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]([CH2:24][CH2:25][C@@:26]([CH3:41])([S:37]([CH3:40])(=[O:39])=[O:38])[C:27]([NH:29][O:30]C4CCCCO4)=[O:28])[C:20](=[O:42])[CH:19]=3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1>CC(O)C>[OH:30][NH:29][C:27](=[O:28])[C@:26]([CH3:41])([S:37]([CH3:40])(=[O:39])=[O:38])[CH2:25][CH2:24][N:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:10][C:7]3[CH:8]=[N:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)=[CH:17][CH:16]=2)=[CH:19][C:20]1=[O:42]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86671961HCID 86671961, compound

Product 1

HCID 86671960(2R)-N-hydroxy-4-[4-{4-[(6-methoxypyridin-3-yl)methoxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

HCl (1.0 N in water, 2.09 mL) was added to a solution of the (2R)-4-[4-{4-[(6-methoxypyridin-3-yl)methoxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (245 mg, 0.418 mmol) in IPA (5.0 mL) for 1 hour. The reaction mixture was concentrated and the residue was triturated with IPA to afford a white suspension at 50° C. for 30 minutes. A white solid was collected by filtration. Yield 215 mg/95% LCMS MS ES-500.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (s, 3 H) 2.07-2.23 (m, 1 H) 2.33-2.43 (m, 1 H) 3.08 (s, 3 H) 3.64-3.79 (m, 1 H) 3.83 (s, 3 H) 4.00-4.12 (m, 1 H) 5.09 (s, 3 H) 6.57-6.67 (m, 2 H) 6.80-6.88 (m, 1 H) 7.05-7.12 (m, 2 H) 7.64-7.73 (m, 3 H) 7.78 (s, 1 H) 8.26 (s, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was triturated with IPA
  3. customto afford a white suspension at 50° C. for 30 minutes
  4. filtrationA white solid was collected by filtration

Sources & evidence

ORD record
ord-88aefc57a93a46c4b54903a8b246da5d
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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