Hydrochloric Acid → 4-Benzylamino-6-[4-methoxybenzyl-(6-morpholinopyridin-3-yl)amino]pyridine-3-carboxylic acid

HRID 2035549Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]([N:20]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:25][CH:26]=2)=[CH:10][C:11]=1[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])C.Cl>C(O)C.[OH-].[Na+].O>[CH2:13]([NH:12][C:11]1[CH:10]=[C:9]([N:20]([CH2:33][C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)[C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:25][CH:26]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3.0 mg of 4-benzylamino-6-[4-methoxybenzyl-(6-morpholinopyridin-3-yl)amino]pyridine-3-carboxylic acid ethylester was dissolved in 1 mL of ethanol, to which 1 mL of 2 mol/L sodium hydroxide in water was added, and stirred at 80° C. for 1 hour. After cooling, hydrochloric acid was added to neutralize the reaction mixture. It was extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated to obtain 3.4 mg of the title compound containing impurities as a brown oil. Without further purification, this was used in the next reaction as it was.

Workup

additionwas added
temperatureAfter cooling
extractionIt was extracted with chloroform
washthe extract was washed with saturated saline
dry with materialdried on anhydrous sodium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-f7456403e9224c0db10419b49e71c533
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575153B2

Reaction notes

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