Triethylamine → HCID 24966553, compound

HRID 1666503Notes

Reaction equation

HRID 1666503 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)[N: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[N: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 20150036Phenyl pyridazin-3-ylcarbamateHCID 66876080HCID 66876080, compound

Product 1

HCID 24966553HCID 24966553, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(3-(piperidin-4-ylidenemethyl)phenoxy)-5-(pyrrolidin-1-yl)pyridine (0.118 g, 0.352 mmol) in DMSO (2 mL) was added phenyl pyridazin-3-ylcarbamate (0.076 g, 0.352 mmol) followed by triethylamine (0.048 mL, 0.352 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 (28% acetone/hexane) to give the title compound (0.125 g, 78% yield). 1H NMR (500 MHz, CDCl3): δ 8.78 (s, 1H), 8.39 (s, 1H), 7.59 (d, J=2.5 Hz, 1H), 7.45 (d, J=4.6 Hz, 1H), 7.27 (m, 2H), 6.95 (m, 1H), 6.92 (m, 2H), 6.84 (m, 2H), 6.38 (s, 1H), 3.69 (m, 2H), 3.58 (m, 2H), 3.27 (m, 4H), 2.59 (m, 2H), 2.45 (m, 2H), 2.03 (m, 4H); 13C NMR (125 MHz, CDCl3): δ 156.56, 153.78, 147.15, 141.50, 138.54, 137.14, 130.50, 129.31, 128.31, 125.21, 123.64, 122.70, 119.41, 117.31, 113.03, 47.85, 45.70, 44.70, 35.76, 29.12, 25.39; m/z (457.1, MH+); HPLC: 97.3%.

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 (28% acetone/hexane)

Sources & evidence

ORD record
ord-1c9355e3d1614dd8ada2ff8f7ad17c0c
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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