Lithium Hydroxide → 6-(6-{[(1,1-Dimethylethoxy)carbonyl]amino}pyridin-2-yl)imidazo[1,2-a]pyridine-2-carboxylic acid

HRID 2363731Notes

Reaction equation

[OH-].[Li+].[CH3:3][C:4]([CH3:37])([O:6][C:7]([N:9](C(OC(C)(C)C)=O)[C:10]1[N:15]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]3[N:20]([CH:22]=[C:23]([C:25]([O:27]CC)=[O:26])[N:24]=3)[CH:21]=2)[CH:13]=[CH:12][CH:11]=1)=[O:8])[CH3:5].O1CCCC1.Cl.Cl>CO>[CH3:5][C:4]([CH3:37])([O:6][C:7]([NH:9][C:10]1[N:15]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]3[N:20]([CH:22]=[C:23]([C:25]([OH:27])=[O:26])[N:24]=3)[CH:21]=2)[CH:13]=[CH:12][CH:11]=1)=[O:8])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

0.9 mL of aqueous 2 M lithium hydroxide solution is added to a solution of 292 mg of ethyl 6-(6-{bis[(1,1-dimethylethoxy)carbonyl]amino}pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxylate in 4.73 mL of a 50/1 mixture of tetrahydrofuran and methanol. The reaction mixture is stirred for 7 hours at 25° C. and then treated dropwise at 0° C. with 2 N hydrochloric acid HCl until a pH of 3 is obtained. The precipitate formed after 20 minutes is filtered off by suction and washed with water (20 mL) and diethyl ether (20 ml) and then dried under reduced pressure to give 195 mg of 6-(6-{[(1,1-dimethylethoxy)carbonyl]amino}pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxylic acid in the form of a beige-coloured solid.

Workup

customis obtained
customThe precipitate formed after 20 minutes
filtrationis filtered off by suction
washwashed with water (20 mL) and diethyl ether (20 ml)
customdried under reduced pressure

Sources & evidence

ORD record: ord-9b65e82609284e68a90440f75c6ea805
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691990B2

Reaction notes

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