Triethylamine → 4-((6-phenoxypyridin-2-yl)methylene)-N-(pyridin-3-yl)piperidine-1-carboxamide

HRID 1666516노트

반응식

HRID 1666516 반응식
F[C:2](F)(F)[C:3](O)=O.N1CCC(=C[C:15]2[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=2)[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)CC1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35](=[O:43])OC2C=CC=CC=2)[CH:29]=1.C([N:46]([CH2:49][CH3:50])[CH2:47][CH3:48])C>CS(C)=O.O>[O:18]([C:19]1[N:20]=[C:21]([CH:2]=[C:3]2[CH2:48][CH2:47][N:46]([C:35]([NH:34][C:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=3)=[O:43])[CH2:49][CH2:50]2)[CH:22]=[CH:23][CH:24]=1)[C:17]1[CH:16]=[CH:15][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66875752HCID 66875752, 화합물

생성물 1

HCID 249662004-((6-phenoxypyridin-2-yl)methylene)-N-(pyridin-3-yl)piperidine-1-carboxamide수율 97%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a solution of 2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate (127.97 mg, 0.480 mmol; Example 91, Step 2) in DMSO (2 mL) was added phenyl pyridin-3-ylcarbamate (102.88 mg, 0.480 mmol) and triethylamine (1.33 mL, 9.6 mmol). The resulting mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and concentrated. The crude compound was purified by silica gel column chromatography (30% acetone/hexane) to give the title compound (180 mg, 97% yield). 1H NMR (500 MHz, CDCl3) δ ppm 8.59 (s, 1H), 8.24-8.14 (m, 3H), 7.70 (t, J=7 Hz, 1H), 7.37 (m, 1H), 7.04-6.98 (m, 5H), 6.93 (d, J=8.5 Hz, 1H), 6.40 (s, 1H), 3.65 (t, J=5.5 Hz, 2H), 3.54 (t, J=5.5 Hz, 2H), 2.61 (t, J=5 Hz, 2H), 2.47 (t, J=5.5 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ ppm 163.64, 154.54, 154.13, 147.75, 140.67, 139.52, 138.86, 137.78, 129.47, 127.82, 125.20, 124.74, 121.46, 119.21, 118.62, 111.71, 45.72, 44.72, 35.76, 29.16; m/z (387.1 MH+); HPLC: 97.66%.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crude compound was purified by silica gel column chromatography (30% acetone/hexane)

출처 및 근거

ORD 기록
ord-a6792474ecec46c791ba2acabcfd8072
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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