Triethylamine → (+/-)-3-Pyridin-2-yl-N-[1-(3-trifluoromethoxyphenyl)ethyl]acrylamide

HRID 2307466ノート

反応式

HRID 2307466 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]([OH:11])=O.[F:12][C:13]([F:25])([F:24])[O:14][C:15]1[CH:16]=[C:17]([CH:21]([NH2:23])[CH3:22])[CH:18]=[CH:19][CH:20]=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]([NH:23][CH:21]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:13]([F:12])([F:24])[F:25])[CH:16]=1)[CH3:22])=[O:11]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 2478243-(2-Pyridyl)acrylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226055421-[3-(Trifluoromethoxy)phenyl]ethan-1-amine

生成物 1

HCID 69919610(+/-)-3-Pyridin-2-yl-N-[1-(3-trifluoromethoxyphenyl)ethyl]acrylamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-(pyridin-2-yl)acrylic acid, Preparation 16 (50 mg) in CH2Cl2 (2 mL) at room temperature were added (±)-1-(3-trifluoromethoxy phenyl)ethylamine, Preparation 15 (76 mg), EDC hydrochloride (129 mg), DMAP (41 mg), and triethylamine (0.2 mL), and the resulting solution was stirred at room temperature for 12 hours. The crude product was purified by silica gel chromatography eluting with ethyl acetate to provide the title compound as the racemate (96 mg). This racemate was separated by HPLC using AD column eluting with hexanes/ethanol (9:1) to give the title compound as an enantiomer of undetermined chirality.

後処理

  1. additionwere added
  2. customThe crude product was purified by silica gel chromatography
  3. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-ab90da8c41264b2190e2bd26b776faf4
出典データセット
uspto-grants-2004_12
特許番号
US06831080B2

反応ノート

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