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

HRID 1666483ノート

反応式

HRID 1666483 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-68281c0f4bcb47c0b00d06654f1ca333
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

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