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

HRID 1428746
ノート
印刷プレビュー

反応式

HRID 1428746 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:14])[C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[C:15]1([CH3:33])[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=[C:23]([C:29]([F:32])([F:31])[F:30])[N:22]=2)[CH:16]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:14])[C:11]([NH:28][CH2:27][C:26]2[C:21]([C:17]3[CH:16]=[C:15]([CH3:33])[CH:20]=[CH:19][CH:18]=3)=[N:22][C:23]([C:29]([F:32])([F:30])[F:31])=[CH:24][CH:25]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 708476592-(3-Chloro-4-cyanophenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

生成物 1

HCID 86680216
2-(3-chloro-4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
収率 88%

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-(3-chloro-4-cyanophenyl)propanoic acid (95 mg, 0.454 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (121 mg, 0.454 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (131 mg, 0.681 mmol), 1-hydroxybenzotriazole (92 mg, 0.681 mmol) and triethylamine (0.16 mL, 1.135 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-(3-chloro-4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (182 mg) was obtained as 88% 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-91607e5b2b1948aeafad9c02a777f2ed
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08937092B2

反応ノート

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