Water → 3H-imidazo[4,5-c]pyridine-6-carboximidamide

HRID 81213Notes

Reaction equation

Cl.[NH2:2]O.C(=O)(O)[O-].[Na+].O.[N:10]1[C:18]2[CH:17]=[C:16]([C:19]#[N:20])[N:15]=[CH:14][C:13]=2[NH:12][CH:11]=1>C(O)C>[N:10]1[C:18]2[CH:17]=[C:16]([C:19](=[NH:2])[NH2:20])[N:15]=[CH:14][C:13]=2[NH:12][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Hydroxylamine hydrochloride (27.2 mg, 0.39 mmol), sodium bicarbonate (49.4 mg, 0.59 mmol), and water (0.392 mL) were combined in a vial and stirred for 15 minutes. This solution was added to a vial containing 4-(5-chloropyridin-3-yl)-2-[(4aR,7aR)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(1R or S)-1-(trans-4-methylcyclohexyl)ethyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (99 mg, 0.196 mmol), dissolved in ethanol (0.915 mL). The mixture was sealed and heated at 100° C. for 1 hour. The reaction was cooled to room temperature, quenched with water, and extracted with ethyl acetate (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 4-(5-chloropyridin-3-yl)-2-[(4aR,7aR)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-N-hydroxy-3-[(1R or S)-1-(trans-4-methylcyclohexyl)ethyl]-3H-imidazo[4,5-c]pyridine-6-carboximidamide. MS ESI calc'd. for C28H36ClN7O2 [M+H]+ 538. found 538.

Workup

additionThis solution was added to
customThe mixture was sealed
temperatureThe reaction was cooled to room temperature
customquenched with water
extractionextracted with ethyl acetate (2×)
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-9750780eae004eba99877ba1f979b9ad
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

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