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 1525441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525441
[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

Komponenten

4

Edukt 1

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

Produkt 1

HCID 709836322-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanolAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cf7a39b7bc87485fb980c48550404c50
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079909B2

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