Hydrochloric Acid → HCID 66558300, compound

HRID 2405945Notes

Reaction equation

HRID 2405945 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[CH:12]=[N:13][N:14]([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])[CH:15]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl>CCO>[C:1]([C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[CH:12]=[N:13][N:14]([CH2:16][CH2:17][C@@:18]([CH3:33])([S:29]([CH3:32])(=[O:30])=[O:31])[C:19]([NH:21][OH:22])=[O:20])[CH:15]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86710249HCID 86710249, compound

Product 1

HCID 66558300HCID 66558300, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-4-{4-[(3-cyanophenyl)ethynyl]-1H-pyrazol-1-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.209 g, 0.444 mmol) in EtOH (40 mL) was added 1M HCl (20 mL). The reaction was allowed to stir at room temperature overnight. The reaction mixture was concentrated, taken back up in MeOH, and concentrated again to give (2R)-4-{4-[(3-cyanophenyl)ethynyl]-1H-pyrazol-1-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (160 mg, 93% yield) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. concentrationconcentrated again

Sources & evidence

ORD record
ord-30e1b45428f74f23bcd714517bb41428
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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