Triethylamine → HCID 24964788, compound

HRID 1666420Notes

Reaction equation

HRID 1666420 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[C:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:13]=2)=[N:9][CH:10]=1)([CH3:3])[CH3:2].[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)[CH:26]=1.C(N(CC)CC)C>CS(C)=O.O>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[CH:18]=[C:19]2[CH2:20][CH2:21][N:22]([C:32]([NH:31][C:27]3[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=3)=[O:33])[CH2:23][CH2:24]2)=[N:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66876070HCID 66876070, compound

Product 1

HCID 24964788HCID 24964788, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 5-isopropoxy-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine (0.18 g, 0.55 mmol) in DMSO (3 mL) was added phenyl pyridin-3-ylcarbamate (0.118 g, 0.55 mmol) followed by triethylamine (0.235 mL, 1.692 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 (30% acetone, 70% hexane) to give the title compound (0.22 g, 89.2%). 1H NMR (500 MHz, CDCl3): δ 8.46 (s, 1H), 8.25 (d, J=3.5 Hz, 1H), 8.02 (d, J=8 Hz, 1H), 7.86 (d, J=3 Hz, 1H), 7.27 (m, 2H), 7.23 (m, 1H), 6.98 (d, J=7.5 Hz, 1H), 6.93 (m, 2H), 6.85 (d, J=9 Hz, 1H), 6.68 (s, 1H), 6.39 (s, 1H), 4.45 (m, 1H), 3.60 (m, 2H), 3.50 (m, 2H), 2.58 (m, 2H), 2.44 (m, 2H), 1.33 (d, J=6 Hz, 6H). 13C NMR (125 MHz, CDCl3): δ 157.34, 155.19, 154.58, 150.73, 143.84, 141.11, 138.80, 137.68, 136.27, 135.56, 129.41, 128.34, 127.50, 124.80, 124.61, 123.60, 120.61, 118.36, 112.49, 71.68, 45.69, 44.71, 35.73, 29.15, 21.96; m/z (445.2, M+ H+); HPLC: 96.0%.

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 (30% acetone, 70% hexane)

Sources & evidence

ORD record
ord-f136f102f105459ba8aa107bfde29398
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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