Triethylamine → 2-tert-Butyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine

HRID 1260317ノート

反応式

HRID 1260317 の反応式
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:3][C:4]#[N:5].C(N(CC)CC)C.Cl.[C:20]([NH:24][NH2:25])([CH3:23])([CH3:22])[CH3:21]>CCO.CCOC(C)=O>[C:20]([N:24]1[C:4]([NH2:5])=[CH:3][C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:25]1)([CH3:23])([CH3:22])[CH3:21]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 115718233-Oxo-3-(pyridin-2-yl)propanenitrile

生成物 1

HCID 672999182-tert-Butyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine収率 62.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 3-oxo-3-pyridin-2-yl-propionitrile (0.40 g, 2.7 mmol; CAS 54123-21-6) at r.t. in EtOH (10 ml) under an argon atmosphere were added triethylamine (1.1 ml, 8.2 mmol) and t-butylhydrazine hydrochloride (1.02 g, 8.2 mmol). The mixture was heated to reflux and stirring was continued for 2 hrs. The orange solution was cooled to r.t. The solids were filtered off. The filtrate was concentrated to leave an orange viscous oil which was taken up in EtOAc and washed with water. The aqueous layer was extracted with EtOAc and with CH2Cl2/MeOH 9:1. The combined organics were dried over MgSO4, filtered and concentrated. After silica gel chromatography using CH2Cl2/MeOH as gradient, the product was obtained as off-white solid (0.366 g, 62%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationThe solids were filtered off
  4. concentrationThe filtrate was concentrated
  5. customto leave an orange viscous oil which
  6. washwashed with water
  7. extractionThe aqueous layer was extracted with EtOAc and with CH2Cl2/MeOH 9:1
  8. dry with materialThe combined organics were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-acda246a8d9440a295ec7f6d081b381e
出典データセット
uspto-grants-2013_06
特許番号
US08470820B2

反応ノート

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