Triethylamine → HCID 24966552, compound

HRID 1666504Notes

Reaction equation

HRID 1666504 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[CH:7][C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[O:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][N:13]=2)[CH2:3][CH2:2]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>[N:18]1([C:15]2[CH:16]=[CH:17][C:12]([O:11][C:10]3[CH:9]=[C:8]([CH:25]=[CH:24][CH:23]=3)[CH:7]=[C:4]3[CH2:5][CH2:6][N:1]([C:33]([NH:32][C:28]4[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=4)=[O:34])[CH2:2][CH2:3]3)=[N:13][CH:14]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66876080HCID 66876080, compound

Product 1

HCID 24966552HCID 24966552, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(3-(piperidin-4-ylidenemethyl)phenoxy)-5-(pyrrolidin-1-yl)pyridine (0.119 g, 0.354 mmol) in DMSO (2 mL) was added phenyl pyridin-3-ylcarbamate (0.076 g, 0.354 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 to give the crude compound. The residue was purified by silica gel column chromatography (32% acetone/hexane) to give the title compound (0.11 g, 68.8% yield). 1H NMR (500 MHz, CDCl3): δ 8.56 (s, 1H), 8.24 (s, 1H), 8.12 (d, J=7.3 Hz, 1H), 7.58 (s, 1H), 7.28 (m, 1H), 6.83 (m, 6H), 6.37 (s, 1H), 3.62 (m, 2H), 3.51 (m, 2H), 3.27 (m, 4H), 2.58 (m, 2H), 2.44 (m, 2H), 2.02 (m, 4H); 13C NMR (125 MHz, CDCl3): δ 156.57, 154.53, 153.74, 143.38, 141.54, 140.80, 138.66, 137.47, 136.49, 130.41, 129.30, 127.70, 124.96, 123.66, 122.73, 119.38, 117.18, 113.11, 47.83, 45.70, 44.75, 41.01, 35.74, 29.71, 29.15, 25.39; m/z (456.2, MH+); HPLC: 97.0%.

Workup

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

Sources & evidence

ORD record
ord-986854771406481496e2b9c113ac18d0
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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