Hydrochloric Acid → HCID 66558215, compound

HRID 2405935Notes

Reaction equation

HRID 2405935 reaction equation
[CH3:1][C@@:2]([S:26]([CH3:29])(=[O:28])=[O:27])([CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N: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:26]([CH3:29])(=[O:28])=[O:27])[CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[CH:17]=[N:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86710243HCID 86710243, compound

Product 1

HCID 66558215HCID 66558215, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(pyrazin-2-yl)-1H-pyrazol-1-yl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.182 g, 0.430 mmol) in EtOH (8 mL) was added 1M HCl (15 mL). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was concentrated, and azeotroped with methanol to remove water to give (2R)—N-hydroxy-2-methyl-2-(methylsulfonyl)-4-[4-(pyrazin-2-yl)-1H-pyrazol-1-yl]butanamide (142 mg, 97% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.49 (s, 3H) 2.21-2.33 (m, 1H) 2.68-2.80 (m, 1H) 3.06 (s, 3H) 4.05-4.15 (m, 1H) 4.22-4.32 (m, 1H) 8.12 (s, 1H) 8.40 (d, J=2.54 Hz, 1H) 8.50 (s, 1H) 8.54 (dd, J=2.54, 1.56 Hz, 1H) 8.96 (d, J=1.56 Hz, 1H) 10.93 (br. s., 1H) 11.14 (s, 1H) LC-MS M+H+340.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customazeotroped with methanol
  3. customto remove water

Sources & evidence

ORD record
ord-b00f4063ed57479ba02266e5a1e714c0
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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