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

HRID 1666516ノート

反応式

HRID 1666516 の反応式
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

参加物

6

反応物 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66875752HCID 66875752、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-a6792474ecec46c791ba2acabcfd8072
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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