Ethanol → Methyl 4-cyclopropyl-5-(3H-imidazo[4,5-c]pyridin-2-yl)-2-methylbenzoate

HRID 1487970Notes

Reaction equation

[CH:1]1([C:4]2[C:13]([CH:14]=O)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:16])[CH:5]=2)[CH2:3][CH2:2]1.[N:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([NH2:24])[CH:18]=1.C(O)C>C(=O)(O)[O-].[Na+]>[CH:1]1([C:4]2[C:13]([C:14]3[NH:24][C:19]4[CH:18]=[N:17][CH:22]=[CH:21][C:20]=4[N:23]=3)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:16])[CH:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

Into a 100-mL round-bottom flask was placed a mixture of methyl 4-cyclopropyl-5-formyl-2-methylbenzoate (compound 87.1, 500 mg, 2.29 mmol), pyridine-3,4-diamine (500 mg, 4.58 mmol), NH4OAc (1.42 g, 18.4 mmol) and ethanol (50 mL). The resulting mixture was stirred open to the air for 3 days at 70° C., then cooled to room temperature and diluted with aqueous sodium bicarbonate (sat., 50 mL). The aqueous phase was extracted with ethyl acetate (2×50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate as the eluent to yield 268 mg (38%) of the title compound as a yellow semi-solid.

Workup

customInto a 100-mL round-bottom flask was placed
temperaturecooled to room temperature
extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
dry with materialthe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography with ethyl acetate as the eluent

Sources & evidence

ORD record: ord-0f440eda1935477abfbf00d5a05b26d0
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

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