Triethylamine → HCID 24966550, compound

HRID 1666508Notes

Reaction equation

HRID 1666508 reaction equation
[N:1]1([C:5]2[CH:6]=[CH:7][C:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[C:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH:13]=3)=[N:9][CH:10]=2)[CH2:4][CH2:3][CH2:2]1.[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>[N:1]1([C:5]2[CH:6]=[CH:7][C:8]([O:11][C:12]3[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=3)[CH:18]=[C:19]3[CH2:20][CH2:21][N:22]([C:32]([NH:31][C:27]4[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=4)=[O:33])[CH2:23][CH2:24]3)=[N:9][CH:10]=2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66876380HCID 66876380, compound

Product 1

HCID 24966550HCID 24966550, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(azetidin-1-yl)-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine (0.098 g, 0.304 mmol) in DMSO (2 mL) was added phenyl pyridin-3-ylcarbamate (0.065 g, 0.304 mmol) followed by triethylamine (0.049 mL, 0.354 mmol). The resulting mixture was stirred at RT for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (32% acetone/hexane) to give the title compound (0.099 g, 73.8% yield). 1H NMR (500 MHz, CDCl3): δ 8.62 (s, 1H), 8.23 (s, 1H), 8.17 (d, J=7.8 Hz, 1H), 7.45 (s, 1H), 7.28 (m, 2H), 7.09 (s, 1H), 6.93 (d, J=7.55 Hz, 1H), 6.88 (m, 3H), 6.80 (m, 1H), 6.37 (s, 1H), 3.87 (t, J=7.05 Hz, 4H), 3.62 (m, 2H), 3.51 (m, 2H), 2.57 (m, 2H), 2.39 (m, 4H); 13C NMR (125 MHz, CDCl3): δ 156.02, 155.42, 154.56, 145.26, 143.28, 140.75, 138.71, 137.58, 136.56, 130.88, 129.34, 127.80, 124.88, 124.01, 123.70, 123.09, 119.85, 117.62, 112.61, 53.85, 53.09, 45.71, 44.75, 35.75, 31.74, 29.71, 29.29, 29.16, 17.52; m/z (442.2, MH+); HPLC: 97.8%.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (32% acetone/hexane)

Sources & evidence

ORD record
ord-46ef6de8f0f540278814a34601550cf8
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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