Triethylamine → 2-(3-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428703ノート

反応式

HRID 1428703 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH3:13])[C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[C:42]1([CH3:60])[CH:47]=[CH:46][CH:45]=[C:44]([C:48]2[C:53]([CH2:54][NH2:55])=[CH:52][CH:51]=[C:50]([C:56]([F:59])([F:58])[F:57])[N:49]=2)[CH:43]=1>O1CCOCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH3:13])[C:10]([NH:55][CH2:54][C:53]2[C:48]([C:44]3[CH:43]=[C:42]([CH3:60])[CH:47]=[CH:46][CH:45]=3)=[N:49][C:50]([C:56]([F:59])([F:57])[F:58])=[CH:51][CH:52]=2)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 532495512-(3-Cyanophenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

生成物 1

HCID 866802072-(3-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide収率 53%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 2-(3-cyanophenyl)propanoic acid (85 mg, 48.8 mmol) in 1,4-dioxane was cooled in an ice bath and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (139 mg, 73.2 mmol), N-hydroxybenzotriazole (98 mg, 73.2 mmol), triethylamine (172 μl, 170 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (130 mg, 48.8 mmol), were added consecutively. The reaction mixture was stirred overnight at room temperature. Water was added to the reaction mixture and extracted with dichloromethane. The combined organic extracts were washed successively with saturated NaHCO3 solution, 0.5 N HCl and then water and dried over magnesium sulfate. Evaporation of the solvent followed by column chromatographic purification afforded the 2-(3-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (110 mg, 53%).

後処理

  1. extractionextracted with dichloromethane
  2. washThe combined organic extracts were washed successively with saturated NaHCO3 solution, 0.5 N HCl
  3. dry with materialwater and dried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customfollowed by column chromatographic purification

出典と根拠

ORDレコード
ord-95cfa4ebf2d040a3a903519252f2b278
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

反応ノート

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