Triethylamine → HCID 24966551, compound

HRID 1666507Notes

Reaction equation

HRID 1666507 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)[N: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[N: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 20150036Phenyl pyridazin-3-ylcarbamateHCID 66876380HCID 66876380, compound

Product 1

HCID 24966551HCID 24966551, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(azetidin-1-yl)-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine (0.045 g, 0.139 mmol) in DMSO (2 mL) was added phenyl pyridazin-3-ylcarbamate (0.03 g, 0.139 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. The residue was purified by silica gel column chromatography (28% acetone/hexane) to give the title compound (0.04 g, 64.5% yield). 1H NMR (500 MHz, CDCl3): δ 8.76 (s, 1H), 8.52 (s, 1H), 7.52 (s, 1H), 7.47 (d, J=2 Hz, 1H), 7.27 (m, 2H), 6.93 (d, J=7.5 Hz, 1H), 6.90 (d, J=8.5 Hz, 1H), 6.86 (m, 2H), 6.80 (m, 1H), 6.39 (s, 1H), 3.88 (t, J=7 Hz, 4H), 3.72 (m, 2H), 3.61 (m, 2H), 2.60 (d, J=6 Hz, 2H), 2.47 (m, 2H), 2.38 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 156.44, 156.01, 155.45, 145.21, 138.58, 137.18, 130.97, 129.35, 125.16, 123.98, 123.06, 119.87, 117.73, 112.55, 53.11, 45.73, 44.73, 35.76, 29.70, 29.12, 17.53; m/z (443.2, MH+); HPLC: 95.0%.

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 (28% acetone/hexane)

Sources & evidence

ORD record
ord-900140e9bd5642abb58a5eb1f45a569f
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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