Diethyl Ether → 4-(phenyl(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)-N-(pyridin-3-yl)piperidine-1-carboxamide

HRID 1666483노트

반응식

HRID 1666483 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=O)[O:9]C2C=CC=CC=2)[CH:2]=1.FC(F)(F)C(O)=O.[C:24]1([C:30](=[C:48]2[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)[C:31]2[CH:32]=[C:33]([CH:45]=[CH:46][CH:47]=2)[O:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][N:36]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.C(OCC)C>CS(C)=O.C(Cl)Cl>[C:24]1([C:30]([C:31]2[CH:47]=[CH:46][CH:45]=[C:33]([O:34][C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:43])([F:44])[F:42])=[CH:37][N:36]=3)[CH:32]=2)=[C:48]2[CH2:53][CH2:52][N:51]([C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:9])[CH2:50][CH2:49]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 866239142-(3-(Phenyl(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetate

생성물 1

HCID 249676374-(phenyl(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)-N-(pyridin-3-yl)piperidine-1-carboxamide

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

반응 조건

온도
60 °C

실험 절차

To a solution of phenyl pyridin-3-ylcarbamate (27.1 mg, 0.127 mmol) in DMSO (3 mL) was added 2-(3-(phenyl(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetate (52 mg, 0.13 mmol), followed by triethylamine (0.018 mL, 0.127 mmol). The reaction was stirred at 60° C. for 3 h and then cooled to RT. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with water and saturated aqueous NH4Cl, dried and concentrated. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl) gave an oil. Diethyether was added followed by CH2Cl2 and the title compound crashed out as a solid (9.2 mg, 13% yield). MS (APCI 10V) AP+ 531.23; 1H NMR (400 MHz, CDCl3) δ ppm 2.43 (t, 2H) 2.50 (t, 2H) 3.51-3.58 (m, 4H) 6.75 (s, 1H) 6.90-6.92 (m, 1H) 6.94-7.04 (m, 2H) 7.12 (dd, 2H) 7.17-7.23 (m, 3H) 7.26-7.37 (m, 3H) 7.86 (dd, 1H) 7.97 (dd, 1H) 8.23 (br. s., 1H) 8.42 (s, 2H).

후처리

  1. temperaturecooled to RT
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous NH4Cl
  4. customdried
  5. concentrationconcentrated
  6. customPurification by silica gel column chromatography (0-5% MeOH/CH2Cl)
  7. customgave an oil

출처 및 근거

ORD 기록
ord-68281c0f4bcb47c0b00d06654f1ca333
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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