Triethylamine → 4-(4-methyl-3-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide

HRID 1666451Notes

Reaction equation

HRID 1666451 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:16]([CH:19]=[C:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][N:6]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)[CH:27]=1.C(N(CC)CC)C>CS(C)=O.O>[CH3:1][C:2]1[CH:18]=[CH:17][C:16]([CH:19]=[C:20]2[CH2:25][CH2:24][N:23]([C:33]([NH:32][C:28]3[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=3)=[O:34])[CH2:22][CH2:21]2)=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:13])([F:12])[F:14])=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 668760202-(2-Methyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

Product 1

HCID 249679974-(4-methyl-3-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamideYield 66.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(2-methyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (440 mg, 0.001 mol) in DMSO (5 mL) was added phenyl pyridin-3-ylcarbamate (278 mg, 0.001 mol) followed by triethylamine (0.4 mL, 0.003 mol). 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 column chromatography (30% acetone-70% hexane) to give the pure title compound (0.310 g, 50%). 1H NMR (500 MHz, CDCl3): δ 8.45-8.42 (m, 2H), 8.26 (d, J=4.5 Hz, 1H), 8.01 (d, J=7 Hz, 1H), 7.91 (d, J=9 Hz, 1H), 7.25-7.22 (m, 1H), 7.05-6.99 (m, 2H), 6.91 (s, 1H), 6.63 (s, 1H), 6.37 (s, 1H), 3.62 (t, J=5.5 Hz, 2H), 3.53 (t, J=11.5 Hz, 2H), 2.63-2.58 (m, 2H), 2.46 (t, J=5.5 Hz, 2H), 2.14 (s, 3H); 13C NMR (125 MHz, CDCl3): δ 165.61, 154.45, 151.24, 145.65, 144.06, 141.14, 137.34, 136.77, 136.49, 136.05, 131.34, 128.95, 127.36, 126.42, 124.45, 123.59, 122.18, 110.76, 45.71, 44.60, 35.69, 29.14, 16.09; m/z (469.5, M+ H+); HPLC: 98.8%.

Workup

  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 column chromatography (30% acetone-70% hexane)

Sources & evidence

ORD record
ord-e5574f0bbc6247c7b0c8006a29d5c7a9
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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