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

HRID 2307466노트

반응식

HRID 2307466 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-ab90da8c41264b2190e2bd26b776faf4
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06831080B2

반응 노트

불러오는 중…