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

HRID 1525440ノート

反応式

HRID 1525440 の反応式
[C:1]([NH:4][C:5]1[N:9]([CH2:10][C:11](OCC)=[O:12])[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:6]=1[C:23]#[C:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C.CO>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:7]2[C:6]([C:23]#[C:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[N:9]([CH2:10][CH2:11][OH:12])[N:8]=2)=[CH:17][CH:18]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 70982686ethyl 2-(5-acetamido-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate

生成物 1

HCID 70983184N-(3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide収率 72.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

To a solution of ethyl 2-(5-acetamido-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate (1 g, 2.5 mmol) in ethanol (40 mL) and methanol (10 ml) was added sodium borohydride (466 mg, 12.3 mmol and the reaction stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 and washed with a dilute NH4Cl solution. The aqueous was extracted with CH2Cl2 and the combined organic extracts were dried over MgSO4, filtered and evaporated. The crude product was suspended in CH2Cl2 (20 ml), heated to reflux, allowed to cool and the product was filtered and dried in vacuo to give N-(3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide as a white solid (659 mg), which was used as such in the subsequent step.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with a dilute NH4Cl solution
  4. extractionThe aqueous was extracted with CH2Cl2
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. temperatureheated
  9. temperatureto reflux
  10. temperatureto cool
  11. filtrationthe product was filtered
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-1a2c612629ee44e8acb989b967371d7a
出典データセット
uspto-grants-2015_07
特許番号
US09079909B2

反応ノート

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