Ethanol → HCID 86721198, compound

HRID 1750360Notes

Reaction equation

HRID 1750360 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23](O)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-:26].[Na+].[CH2:28]([OH:30])[CH3:29]>C1COCC1>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([N:5]3[CH2:9][CH2:8][CH:29]([C:28]([OH:26])=[O:30])[CH2:2][CH2:1]3)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 867211822-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid

Product 1

HCID 86721198HCID 86721198, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid (95 mg, 0.19 mmol) and 1N aqueous sodium hydroxide solution (0.286 mL, 0.29 mmol) in ethanol (2 mL) and THF (2 mL) was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and water and 1N hydrochloric acid were added to the residue. After extraction with ethyl acetate, washing with water and saturated brine and drying, the solvent was evaporated under reduced pressure to give the title compound (74 mg, 0.157 mmol, 83%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water and 1N hydrochloric acid
  2. additionwere added to the residue
  3. extractionAfter extraction with ethyl acetate
  4. washwashing with water and saturated brine
  5. customdrying
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4a86ef33868942bfb82fffecca25df0e
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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