Imidazole → HCID 71547903, compound

HRID 1497438Notes

Reaction equation

CS(O[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:24])[NH:22][CH3:23])=[CH:17][CH:16]=2)=[CH:11][N:10]=1)[CH2:7][CH3:8])(=O)=O.[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.C(N(CC)CC)C>C(Cl)Cl>[N:25]1([CH:6]([C:9]2[N:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([NH:22][CH3:23])=[O:24])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:7][CH3:8])[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-(5-(4-(methylcarbamoyl)phenyl)pyridin-2-yl)propyl methanesulfonate (0.02 g, 0.057 mmol), 1H-imidazole (0.008 g, 0.114 mmol) and triethylamine (0.03 mL, 0.114 mmol) in DCM (10 mL) was stirred and refluxed at 50° C. for 3 h. The mixture was then cooled to room temperature, poured out into ice water (50 mL) and extracted with DCM (2×50 mL). The organic layer was separated, dried (Na2SO4), and the solvent was evaporated under vacuo. The resulting residue was purified by preparative TLC using 5% methanol in dichloromethane and the product isolated as off white solid (0.007 g, 39% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.91 (d, 1H), 8.46 (d, 1H), 8.12 (d, 1H), 7.91 (d, 2H), 7.80 (d, 3H), 7.39 (d, 1H), 7.31 (s, 1H), 6.89 (s, 1H), 5.37 (t, 1H), 2.78 (d, 3H), 2.27 (m, 2H), 0.89 (t, 3H). LC-MS: m/z 321.5 [M+H]+.

Workup

temperatureThe mixture was then cooled to room temperature
extractionextracted with DCM (2×50 mL)
customThe organic layer was separated
dry with materialdried (Na2SO4)
customthe solvent was evaporated under vacuo
customThe resulting residue was purified by preparative TLC

Sources & evidence

ORD record: ord-1a30cd74d9fc432db2ca67996fcec64d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199975B2

Reaction notes

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