Sodium Hydroxide → HCID 86721243, compound

HRID 1750399Notes

Reaction equation

HRID 1750399 reaction equation
[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([O:19]CC)=[O:18])[N:15]=1.[OH-].[Na+]>C(O)C.C1COCC1>[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[N:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86721242HCID 86721242, compound

Product 1

HCID 86721243HCID 86721243, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of the compound (2.55 g, 6.85 mmol) obtained in step 6 and 1N aqueous sodium hydroxide solution (10.27 mL, 10.27 mmol) in ethanol (10 mL) and THF (10 ml) was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. 1N Hydrochloric acid was added thereto, and the precipitate was collected by filtration, and washed with diethyl ether and hexane to give 2-(2-(5-bromo-1-tert-butyl-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid (2.23 g, 6.48 mmol, 95%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. addition1N Hydrochloric acid was added
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with diethyl ether and hexane

Sources & evidence

ORD record
ord-b9f167ac076948f5b877a85b04577ccb
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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