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 1525441노트

반응식

HRID 1525441 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cf7a39b7bc87485fb980c48550404c50
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079909B2

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