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

HRID 1666413Notes

Reaction equation

HRID 1666413 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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%.

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 silica gel column chromatography (38% acetone, 62% hexane)

Sources & evidence

ORD record
ord-2d04ea050f2249e49322b44e0792d6ea
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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