Hydrochloric Acid → HCID 90403801, compound

HRID 1049267Notes

Reaction equation

[CH:1]([C:4]1[N:5](COCCOC)[C:6]([C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:17]=[N:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)[CH:12]=[CH:11][N:10]=2)=[CH:7][N:8]=1)([CH3:3])[CH3:2].Cl>O1CCOCC1>[CH:1]([C:4]1[NH:5][C:6]([C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:17]=[N:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)[CH:12]=[CH:11][N:10]=2)=[CH:7][N:8]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 2-(2-isopropyl-1-((2-methoxyethoxy)methyl)-1H-imidazol-5-yl)-4-((6-nitropyridin-3-yl)oxy)pyridine (783 mg, 1.894 mmol) in dioxane (15 mL) was treated with 6N HCl (9.0 mL), heated at 50° C. for 16 h, then cooled to RT and evaporated to remove most of the organics. The aqueous residue was treated with EtOAc, made basic with 1N NaOH, the layers separated and the aqueous layer extracted with additional EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 2-(2-isopropyl-1H-imidazol-5-yl)-4-((6-nitropyridin-3-yl)oxy)pyridine (612 mg, 99%). 1H NMR (400 MHz, DMSO-d6): δ 12.01 (s, 1H), 8.58 (d, J=2.8 Hz, 1H), 8.47 (d, J=5.6 Hz, 1H), 8.41 (d, J=8.9 Hz, 1H), 7.95 (dd, J=8.9, 2.8 Hz, 1H), 7.61 (d, J=2.1 Hz, 1H), 7.45 (d, J=2.5 Hz, 1H), 6.97 (dd, J=5.4, 2.7 Hz, 1H), 2.95-2.94 (m, 1H), 1.23 (t, J=6.9 Hz, 6H); MS (ESI) m/z: 326.1 (M+H+).

Workup

temperaturecooled to RT
customevaporated
customto remove most of the organics
additionThe aqueous residue was treated with EtOAc
customthe layers separated
extractionthe aqueous layer extracted with additional EtOAc
washThe combined organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-9ac2020ee8a24a7eb0a0ba16fbbdc258
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382228B2

Reaction notes

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