Hydrochloric Acid → HCID 178448473, compound

HRID 709289Notes

Reaction equation

HRID 709289 reaction equation
[F:1][C:2]([F:42])([C@H:35]1[CH2:40][CH2:39][C@H:38]([OH:41])[CH2:37][CH2:36]1)[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C@@:18]([CH3:33])([S:29]([CH3:32])(=[O:31])=[O:30])[C:19]([NH:21][O:22]C3CCCCO3)=[O:20])[C:12](=[O:34])[CH:11]=2)=[CH:6][CH:5]=1.Cl.CO>ClCCl.O1CCOCC1>[F:42][C:2]([F:1])([C@H:35]1[CH2:36][CH2:37][C@H:38]([OH:41])[CH2:39][CH2:40]1)[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C@@:18]([CH3:33])([S:29]([CH3:32])(=[O:31])=[O:30])[C:19]([NH:21][OH:22])=[O:20])[C:12](=[O:34])[CH:11]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178448472HCID 178448472, compound

Product 1

HCID 178448473HCID 178448473, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (2R)-4-[4-{4-[difluoro(trans-4-hydroxycyclohexyl)methoxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (280 mg, 0.473 mM) in 2.3 mL of dichloromethane was added a solution of 4 M HCl in dioxane (0.120 mL, 0.473 mM). The reaction mixture was allowed to stir for 20 minutes before being treated with 0.5 mL of MeOH. Reaction was concentrated in vacuo and purified by reverse phase (Shimadzu) prep HPLC 35 mg, (14%). LCMS 529.1 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.30 (br. s., 2H) 1.40-1.54 (m, 2H) 1.64-1.74 (m, 3H) 1.99-2.14 (m, 4H) 2.31-2.42 (m, 1H) 2.51-2.67 (m, 1H) 3.09 (s, 3H) 3.45-3.62 (m, 1H) 3.87-4.02 (m, 1H) 4.23-4.34 (m, 1H) 6.70-6.75 (m, 1H) 6.78 (s, 1H) 7.21-7.33 (m, 2H) 7.65-7.74 (m, 3H)

Workup

  1. customReaction
  2. concentrationwas concentrated in vacuo
  3. custompurified by reverse phase (Shimadzu)

Sources & evidence

ORD record
ord-5efb8bde0627464faaa8d1b1e387fcac
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

Loading…