Triethylamine → 2-(4-Cyano-3-methoxyphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428754ノート

反応式

HRID 1428754 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=O)=[CH:5][C:4]=1[O:14][CH3:15])#[N:2].[C:16]1([CH3:34])[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=[C:24]([C:30]([F:33])([F:32])[F:31])[N:23]=2)[CH:17]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([NH:29][CH2:28][C:27]2[C:22]([C:18]3[CH:17]=[C:16]([CH3:34])[CH:21]=[CH:20][CH:19]=3)=[N:23][C:24]([C:30]([F:33])([F:31])[F:32])=[CH:25][CH:26]=2)=[O:12])=[CH:5][C:4]=1[O:14][CH3:15])#[N:2]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 708475882-(4-Cyano-3-methoxyphenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

生成物 1

HCID 866802192-(4-Cyano-3-methoxyphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide収率 90%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2-(4-cyano-3-methoxyphenyl)propanoic acid (112 mg, 0.545 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (145 mg, 0.546 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (157 mg, 0.819 mmol), N-hydroxybenzotriazole (111 mg, 0.819 mmol) and triethylamine (0.19 mL, 1.36 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-Cyano-3-methoxyphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (222 mg) was obtained as 90% yield.

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-e1e652aa6d32412ea10ebff1dd1a512a
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

反応ノート

読み込み中…