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

HRID 709282Notes

Reaction equation

HRID 709282 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[N:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][N:17]([CH2:20][CH2:21][C@@:22]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[C:23]([NH:25][O:26]C4CCCCO4)=[O:24])[C:16](=[O:38])[CH:15]=3)=[CH:10][CH:9]=2)[N:4]=1.ClCCl.O.Cl>O1CCOCC1>[OH:26][NH:25][C:23](=[O:24])[C@:22]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:21][CH2:20][N:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([N:5]3[N:4]=[C:3]([O:2][CH3:1])[CH:7]=[N:6]3)=[CH:9][CH:10]=2)=[CH:15][C:16]1=[O:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 86671958(2R)-4-{4-[4-(4-methoxy-2H-1,2,3-triazol-2-yl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86671959(2R)-N-hydroxy-4-{4-[4-(4-methoxy-2H-1,2,3-triazol-2-yl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To (2R)-4-{4-[4-(4-methoxy-2H-1,2,3-triazol-2-yl)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (120 mg, 0.22 mmol) was added dioxane (2 ml), dichloromethane (2 ml), and water (1 ml). The reaction flask was cooled externally with ice then treated with a 4.0M sol of HCl in dioxane (0.55 ml). The reaction mixture was stirred for 15 minutes then concentrated under reduced pressure. IPA (10 ml) was added and concentrated to azeotrope any remaining water to furnish a tan solid (80 mg, 80% TY). MS (LC/MS) m/z 462.3 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.74 (s, 3H) 2.34-2.51 (m, 1H) 2.55-2.81 (m, 1H) 3.13 (s, 3H) 3.96-4.06 (m, 1H) 4.07 (s, 3H) 4.26-4.45 (m, 1H) 6.84-7.00 (m, 2H) 7.49 (s, 1H) 7.75-7.93 (m, 3H) 8.09 (d, J=8.78 Hz, 2H)

Workup

  1. temperatureThe reaction flask was cooled externally with ice
  2. concentrationthen concentrated under reduced pressure
  3. additionIPA (10 ml) was added
  4. concentrationconcentrated
  5. customto furnish a tan solid (80 mg, 80% TY)

Sources & evidence

ORD record
ord-799b794a40e04422b39d7e9f7d316b90
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

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