Hydrochloric Acid → HCID 66558216, compound

HRID 2405938Notes

Reaction equation

HRID 2405938 reaction equation
[CH3:1][C@@:2]([S:30]([CH3:33])(=[O:32])=[O:31])([CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:29]=[N:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[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:30]([CH3:33])(=[O:32])=[O:31])[CH2:13][CH2:14][N:15]1[CH:19]=[C:18]([C:20]2[CH:29]=[N:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH:17]=[N:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86710245HCID 86710245, compound

Product 1

HCID 66558216HCID 66558216, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(quinoxalin-2-yl)-1H-pyrazol-1-yl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.685 g, 1.62 mmol, 1 eq) in EtOH (8 mL) was added 1M HCl (4 mL). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was concentrated and azeotroped with MeOH to remove water to give (2R)—N-hydroxy-2-methyl-2-(methylsulfonyl)-4-[4-(quinoxalin-2-yl)-1H-pyrazol-1-yl]butanamide (38 mg, 86% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 1.51 (s, 3H) 2.26-2.37 (m, 1H) 2.72-2.85 (m, 1H) 3.07 (s, 3H) 4.10-4.20 (m, 1H) 4.27-4.38 (m, 1H) 7.73 (s, 1H) 7.80 (s, 1H) 7.98 (d, J=8.39 Hz, 1H) 8.02 (d, J=0.78 Hz, 1H) 8.31 (s, 1H) 8.72 (s, 1H) 9.30 (s, 1H) 10.23 (s, 1H) 11.01 (br. s., 1H). LC-MS M+H+390.1.

Workup

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

Sources & evidence

ORD record
ord-17944d20cf754aee8a1dc9c7449f7716
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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