Triethylamine → 2-Chloro-N-(3-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]phenyl)nicotinamide

HRID 2371062노트

반응식

HRID 2371062 반응식
[O:1]=[C:2]([NH:18][CH:19]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)[C:20]([F:23])([F:22])[F:21])/[CH:3]=[CH:4]/[C:5]1[CH:13]=[CH:12][C:8](C(O)=O)=[C:7](C(F)(F)F)[CH:6]=1.C([N:36](CC)CC)C.[Cl:41][C:42]1[N:50]=[CH:49][CH:48]=[CH:47][C:43]=1[C:44](Cl)=[O:45]>ClC(Cl)Cl.ClCCl>[Cl:41][C:42]1[N:50]=[CH:49][CH:48]=[CH:47][C:43]=1[C:44]([NH:36][C:7]1[CH:8]=[CH:12][CH:13]=[C:5](/[CH:4]=[CH:3]/[C:2](=[O:1])[NH:18][CH:19]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[C:20]([F:23])([F:22])[F:21])[CH:6]=1)=[O:45]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 866530664-[(1E)-3-Oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzoic acid

생성물 1

HCID 866893332-Chloro-N-(3-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]phenyl)nicotinamide

시약·촉매·용매 2

HCID 6212Chloroform용매2회HCID 6344Dichloromethane용매

실험 절차

100 mg (0.25 mmol) of (2E)-3-(3-aminophenyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]-ethyl}acrylamide from Example 3, Stage 2 and 33.8 mg (0.33 mmol) of triethylamine were initially charged in 1 ml of trichloromethane, and a solution of 49.8 mg (0.33 mmol) of 2-chloronicotinoyl chloride in 1 ml of trichloromethane was added. The reaction solution was stirred at room temperature for 18 hours, then diluted with dichloromethane, washed three times with water and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue purified by preparative HPLC (solvent=water (A)+acetonitrile (B), gradient=40 min, from 10% B to 100% B, flow=18 ml/min).

후처리

  1. washwashed three times with water
  2. dry with materialdried over sodium sulphate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue purified by preparative HPLC (solvent=water (A)+acetonitrile (B), gradient=40 min, from 10% B to 100% B, flow=18 ml/min)

출처 및 근거

ORD 기록
ord-2e4a0ed75e7d46709aaaefea9c7a269b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710242B2

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