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

HRID 1666516Notes

Reaction equation

HRID 1666516 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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%.

Workup

  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)

Sources & evidence

ORD record
ord-a6792474ecec46c791ba2acabcfd8072
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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