Imidazole → HCID 71547996, compound

HRID 1497469Notes

Reaction equation

HRID 1497469 reaction equation
CS(O[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]#[N:22])=[CH:11][N:10]=1)[CH2:7][CH3:8])(=O)=O.C(N(CC)CC)C.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>C(Cl)Cl.O>[N:30]1([CH:6]([C:9]2[N:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]#[N:22])=[CH:13][CH:14]=2)[CH2:7][CH3:8])[CH:34]=[CH:33][N:32]=[CH:31]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 8471TriethylamineHCID 86680633HCID 86680633, compound

Product 1

HCID 71547996HCID 71547996, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To solution of 1-(5-(2-cyanophenyl)pyridin-2-yl)propyl methanesulfonate (0.050 g, 0.15 mmol) in DCM was added triethyl amine (0.030 g, 0.30 mmol) followed by imidazole (0.20 g, 0.30 mmol) at room temperature. The reaction mixture was stirred for 12 h at room temperature. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (50 mL). The organic extracts were dried over sodium sulphate, filtered and concentrated to obtain the crude compound which was purified by preparative TLC by using 5% MeOH/DCM to give 2-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)benzonitrile (10 mg, 24%). 1H NMR (400 MHz DMSO-d6): δ 8.77 (s, 1H), 8.04 (dd, 1H), 7.98 (d, 1H), 7.84 (s, 1H), 7.80 (d, 1H), 7.68 (d, 1H), 7.63 (t, 1H), 7.44 (d, 1H), 7.34 (s, 1H), 6.92 (s, 1H), 5.43 (dd, 1H), 2.31-2.20 (m, 2H), 0.83 (t, 3H); LC-MS m/z calcd for [M+H]+ 289.14. found 289.5.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialThe organic extracts were dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain the crude compound which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-52421f1bd1f34b97a4948fd0d3e8f5c7
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

Loading…