Hydrochloric Acid → HCID 66558301, compound

HRID 2405949Notes

Reaction equation

HRID 2405949 reaction equation
[CH3:1][C@@:2]([S:31]([CH3:34])(=[O:33])=[O:32])([CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[O:27][CH:28]=[CH:29][N:30]=3)=[CH:22][CH:21]=2)[CH:17]=[N:16]1)[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl>CCO>[OH:6][NH:5][C:3](=[O:4])[C@:2]([CH3:1])([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[O:27][CH:28]=[CH:29][N:30]=3)=[CH:22][CH:21]=2)[CH:17]=[N:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86710250HCID 86710250, compound

Product 1

HCID 66558301HCID 66558301, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-{4-[4-(1,3-oxazol-2-yl)phenyl]-1H-pyrazol-1-yl}-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.031 g, 0.063 mmol) in EtOH (20 mL) was added 6M HCl (5 mL). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated and was purified via reverse-phase chromatography, using 5%-95% acetonitrile/water with 0.1% formic acid modifier. The target fractions were combined and evaporated to give (2R)—N-hydroxy-2-methyl-2-(methylsulfonyl)-4-{4-[4-(1,3-oxazol-2-yl)phenyl]-1H-pyrazol-1-yl}butanamide (6 mg, 20% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 1.22-1.30 (m, 3H), 2.44-2.59 (m, 1H), 2.76-2.92 (m, 1H), 2.94-3.11 (m, 3H), 4.19-4.45 (m, 2H), 7.23 (s, 1H), 7.45-7.56 (m, 2H), 7.66-7.74 (m, 2H), 7.80-7.86 (m, 1H), 7.93-8.06 (m, 2H). LC-MS M+H+405.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwas purified via reverse-phase chromatography
  3. customevaporated

Sources & evidence

ORD record
ord-7e7825dd95244f9ab3ac255b0e22071e
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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