Hydrochloric Acid → 6-(3-Ethylureido)-4-(pyridin-3-ylmethylamino)nicotinic acid

HRID 2174227Notes

Reaction equation

[OH-].[Li+].[CH2:3]([NH:5][C:6](=[O:27])[NH:7][C:8]1[CH:18]=[C:17]([NH:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][N:9]=1)[CH3:4].Cl>O.CCO>[CH2:3]([NH:5][C:6](=[O:27])[NH:7][C:8]1[CH:18]=[C:17]([NH:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1)[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

Lithium hydroxide (0.310 g, 7.29 mmol) dissolved in water (2 mL) was added to a solution of iv (0.250 g, 0.730 mmol) in EtOH (2 mL) THF (5 mL). The mixture was warmed to 60° C. for 3 h, cooled to room temperature and reduced in vacuo. The resulting residue was re-dissolved in water (2 mL) and the pH adjusted to pH 2-3 using conc. HCl (35%). The resulting colourless precipitate was filtered, washed with water and dried in vacuo to give vi (0.219 g, 0.695 mmol, 95%) as a colourless powder. 1H NMR (300 MHz, DMSO-d6): δ 9.10 (1H, s), 8.65-8.57 (2H, m), 8.07 (1H, br), 7.75 (1H, dt, J 8.2 and 1.5), 7.38 (1H, dd, J 7.7 and 4.6), 6.64 (1H, s), 4.45 (2H, d, J 6.1), 3.14 (2H, dq, J 7.2 and 5.6), 1.05 (3H, t, J 7.2); [M+H]+ m/z=316.1.

Workup

temperaturecooled to room temperature
filtrationThe resulting colourless precipitate was filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-742a711d005648b091687f1dc4b0fd1e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09060515B2

Reaction notes

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