Hydrochloric Acid → N-hydroxy-2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanamide

HRID 533554Notes

Reaction equation

HRID 533554 reaction equation
[CH3:1][C:2]([S:26]([CH3:29])(=[O:28])=[O:27])([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)=[CH:17][CH:16]=1)[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl.CO>C(Cl)Cl>[OH:6][NH:5][C:3](=[O:4])[C:2]([CH3:1])([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 866687732-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 51355578N-hydroxy-2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (302.9 mg, 0.719 mmol) was dissolved in methylene chloride (10 mL) at ambient temperature. To this solution was added HCl (4M in 1,4-dioxane, 5.39 mL, 21.6 mmol) and the solution was stirred at RT for 5 minutes. Methanol (500 uL) was added followed by silica gel and the mixture was concentrated to dryness. The crude material was purified via silica gel chromatography eluting with methylene chloride/methanol to afford N-hydroxy-2-methyl-2-(methylsulfonyl)-4-[4-(1H-pyrazol-1-yl)phenyl]butanamide as a solid. 67.8 mg. LCMS: (M−1) 336.3 1H NMR (CD3OD) 8.16 (1H, d, J=2.54 Hz), 7.69 (1H, d, J=1.17 Hz), 7.64 (2H, d, J=8.59), 7.36 (2H, d, J=8.40) 6.50 (1H, t), 3.03 (3H, s), 2.80-2.72 (1H, m), 2.61-2.52 (2H, m), 2.11-2.03 (1H, m), 1.65 (3H, s) ppm.

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. customThe crude material was purified via silica gel chromatography
  3. washeluting with methylene chloride/methanol

Sources & evidence

ORD record
ord-3d3c9be5115841e7bc4cbb01bc752897
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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