Triethylamine → 4-(3-(5-ethoxypyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide

HRID 1666413노트

반응식

HRID 1666413 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[C:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:12]=2)=[N:8][CH:9]=1)[CH3:2].[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31](=O)[O:32]C2C=CC=CC=2)[N:25]=1.C(N(CC)CC)C>CS(C)=O.O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[CH:17]=[C:18]2[CH2:23][CH2:22][N:21]([C:31]([NH:30][C:26]3[N:25]=[N:24][CH:29]=[CH:28][CH:27]=3)=[O:32])[CH2:20][CH2:19]2)=[N:8][CH:9]=1)[CH3:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 20150036Phenyl pyridazin-3-ylcarbamateHCID 668759965-Ethoxy-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine

생성물 1

HCID 249647854-(3-(5-ethoxypyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide수율 73.7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a solution of 5-ethoxy-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine (0.22 g, 0.708 mmol) in DMSO (4 mL) was added phenyl pyridazin-3-ylcarbamate (0.152 g, 0.708 mmol) followed by triethylamine (0.265 mL, 2.12 mmol). The resulting mixture was stirred at RT for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (38% acetone, 62% hexane) to give the title compound (0.225 g, 73% yield). 1H NMR (500 MHz, CDCl3): δ 8.80 (s, 1H), 8.29 (s, 1H), 7.87 (d, J=3.0 Hz, 1H), 7.41 (d, J=4.0 Hz, 1H), 7.34-7.23 (m, 1H), 6.99-6.93 (m, 3H), 6.86 (d, J=9.0 Hz, 1H), 6.39 (s, 1H), 4.02 (q, J=7.0 Hz, 2H), 3.67 (s, 2H), 3.57 (s, 2H), 2.6-2.5 (m, 2H), 2.47 (m, 2H), 1.40 (t, J=7.0 Hz, 3H). 13C NMR (125 MHz, CDCl3): δ 157.32, 156.79, 155.24, 151.82, 147.4, 138.74, 137.55, 133.57, 129.40, 127.97, 126.82, 124.89, 124.56, 120.55, 118.91, 112.52, 64.61, 45.66, 44.66, 35.78, 29.14, 14.82; m/z (432.1, M+ H+); HPLC: 98.76%.

후처리

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (38% acetone, 62% hexane)

출처 및 근거

ORD 기록
ord-2d04ea050f2249e49322b44e0792d6ea
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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