1,2-Dichloroethane → (4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol

HRID 1941884ノート

反応式

HRID 1941884 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([OH:18])=O)[CH:9]=[N:8]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.O[NH:43][C:44](=[NH:53])[C:45]1[CH:50]=[CH:49][C:48]([CH2:51][OH:52])=[CH:47][CH:46]=1.Cl>CN(C=O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:13])([F:14])[F:15])=[C:10]([C:16]2[O:18][N:53]=[C:44]([C:45]3[CH:50]=[CH:49][C:48]([CH2:51][OH:52])=[CH:47][CH:46]=3)[N:43]=2)[CH:9]=[N:8]1

参加物

9

反応物 6

HCID 111,2-Dichloroethane2 回HCID 313Hydrochloric AcidHCID 757711-Hydroxybenzotriazole2 回HCID 81531Diisopropylethylamine2 回HCID 167877231-(2-Pyridinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidHCID 178513316HCID 178513316、化合物

生成物 1

HCID 66996907(4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (2.57 g, 9.99 mmol) in DMF (30 mL) was added EDC (2.395 g, 12.49 mmol), HOBt (1.913 g, 12.49 mmol) and Hunig's Base (5.24 mL, 30.0 mmol). The reaction was stirred for 40 min. at room temperature, then N-hydroxy-4-(hydroxymethyl)benzimidamide, Int.2, (2.076 g, 12.49 mmol) was added. The reaction mixture was stirred at room temperature for 7 h, then additional EDC (2.395 g, 12.49 mmol), HOBt (1.913 g, 12.49 mmol) and Hunig's Base (5.24 mL, 30.0 mmol) were added. The reaction was heated to 60° C. for 2 h, then at 110° C. for 10 min. 1N aq. HCl was added to adjust the pH to 1, then 30 mL of water was added. The resulting precipitated product was collected by filtration and washed with water to afford (4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol (2.28 g, 5.83 mmol, 58%) as a light yellow solid.

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 7 h
  2. temperatureThe reaction was heated to 60° C. for 2 h
  3. waitat 110° C. for 10 min
  4. customThe resulting precipitated product
  5. filtrationwas collected by filtration
  6. washwashed with water

出典と根拠

ORDレコード
ord-8051eedff57d4b2a9774cd314f2cbe34
出典データセット
uspto-grants-2013_03
特許番号
US08389509B2

反応ノート

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