Imidazole → HCID 71547905, compound

HRID 1497446Notes

Reaction equation

CS(O[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH2:23][O:24][CH3:25])=[CH:17][CH:16]=2)=[CH:11][N:10]=1)[CH2:7][CH3:8])(=O)=O.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1.C(N(CC)CC)C>C1COCC1>[N:26]1([CH:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH2:23][O:24][CH3:25])=[CH:17][CH:16]=3)=[CH:11][N:10]=2)[CH2:7][CH3:8])[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-(5-(4-((methoxymethoxy)methyl)phenyl)pyridin-2-yl)propyl methanesulfonate (0.1 g, 0.27 mmol), 1H-imidazole (0.037 g, 0.54 mmol) and triethylamine (0.07 mL, 0.54 mmol) in THF (15 mL) was stirred and refluxed at 65° C. for 12 h, cooled to room temperature, poured into ice water (50 mL) and extracted with EtOAc (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 isolated as light green viscous liquid (0.04 g, 44% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.86 (s, 1H), 8.06 (dd, 1H), 7.81 (s, 1H), 7.69 (d, 2H), 7.44 (d, 2H), 7.37 (d, 1H), 7.30 (s, 1H), 5.36 (q, 1H), 4.65 (s, 2H), 4.56 (s, 2H), 3.30 (s, 3H), 2.25 (m, 2H), 0.81 (t, 3H). LC-MS: m/z 338.2 [M+H]+.

Workup

temperaturecooled to room temperature
extractionextracted with EtOAc (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-381f0cddb1a14c539899b12ad33c2b87
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199975B2

Reaction notes

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