Hydrochloric Acid → HCID 178448473, compound

HRID 1184014Notes

Reaction equation

HRID 1184014 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-0c233d2facf443b6b515d4637257241f
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Reaction notes

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