Hydrochloric Acid → HCID 86670660, compound

HRID 468654Notes

Reaction equation

HRID 468654 reaction equation
Cl.[F:2][C:3]1([F:38])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]3[C:17]([F:18])=[CH:16][N:15]([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:14](=[O:37])[CH:13]=3)=[CH:11][C:5]=2[O:4]1>C(O)C.O>[F:38][C:3]1([F:2])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]3[C:17]([F:18])=[CH:16][N:15]([CH2:19][CH2:20][C@@:21]([CH3:36])([S:32]([CH3:35])(=[O:34])=[O:33])[C:22]([NH:24][OH:25])=[O:23])[C:14](=[O:37])[CH:13]=3)=[CH:11][C:5]=2[O:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86670661HCID 86670661, compound

Product 1

HCID 86670660HCID 86670660, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Aqueous HCl (1.42 mL, 1.42 mmol) was added to a solution of (2R)-4-[4-(2,2-Difluoro-1,3-benzodioxol-5-yl)-5-fluoro-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (259 mg, 0.474 mmol) in ethanol (5 mL) and water (2 mL) and the reaction was stirred overnight at rt. The solid was collected via filtration, washed with water (5×3 mL) and dried under reduced pressure to afford the title compound (143 mg, 65.3%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (s, 3H) 2.07-2.24 (m, 1H) 2.36-2.49 (m, 1H) 3.11 (s, 3H) 3.68-3.86 (m, 1H) 3.98-4.13 (m, 1H) 6.58 (d, J=7.61 Hz, 1H) 7.36-7.49 (m, 1H) 7.55 (d, J=8.39 Hz, 1H) 7.68 (s, 1H) 8.06 (d, J=6.63 Hz, 1H) 9.24 (br. s., 1H) 11.08 (s, 1H).

Workup

  1. filtrationThe solid was collected via filtration
  2. washwashed with water (5×3 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-0173d0581dc6428a9df71fd0e5fe64cb
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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