N-(3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide → 2-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanol

HRID 1775577Notes

Reaction equation

HRID 1775577 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([NH:21]C(=O)C)[N:10]([CH2:25][CH2:26][OH:27])[N:9]=2)=[CH:4][CH:3]=1>C(O)C.[OH-].[Na+]>[NH2:21][C:11]1[N:10]([CH2:25][CH2:26][OH:27])[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:12]=1[C:13]#[C:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 70983184N-(3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide

Product 1

HCID 709836322-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanolYield 36.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-(3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide (382 mg, 1.05 mmol) in ethanol (4 mL) and 25% NaOH (6 mL) was heated to 83° C. for 16 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate twice and the organic phases combined, dried over MgSO4, filtered and evaporated, purification using chromatography (silica gel, gradient 0 to 10% methanol/CH2Cl2) gave 2-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanol as a solid (122 mg), which was used as such in the subsequent step.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe aqueous phase was washed with ethyl acetate twice
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurification

Sources & evidence

ORD record
ord-9c8bf0d2bdd645898bbc8b16a2c862cf
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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