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

HRID 1428754노트

반응식

HRID 1428754 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e1e652aa6d32412ea10ebff1dd1a512a
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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