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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 1475890
Notes
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Reaction equation

HRID 1475890 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-4c8656e233b047159a9e2383b827e658
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09018384B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes