Sodium Hydroxide → HCID 86721262, compound

HRID 1750417Notes

Reaction equation

HRID 1750417 reaction equation
[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([C:19]3[S:20][CH:21]=[C:22]([CH2:24][C:25]([O:27]CC)=[O:26])[N:23]=3)[CH:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C.C1COCC1>[CH:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)=[C:10]([C:19]3[S:20][CH:21]=[C:22]([CH2:24][C:25]([OH:27])=[O:26])[N:23]=3)[CH:9]=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86721261HCID 86721261, compound

Product 1

HCID 86721262HCID 86721262, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of the compound (269 mg, 0.65 mmol) obtained in step 3 and 1N aqueous sodium hydroxide solution (0.976 mL, 0.98 mmol) in ethanol (4 mL) and THF (4 mL) was stirred at room temperature for 3 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 crystallized from diethyl ether and hexane to give 2-(2-(1-cyclohexyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid (226 mg, 0.586 mmol, 90%) 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. customcrystallized from diethyl ether and hexane

Sources & evidence

ORD record
ord-2b2da426d6294b95b5d2ef6704452041
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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