Lithium hydroxide, monohydrate → 4-[3-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-ylsulfanyl]-butyric acid

HRID 215979Notes

Reaction equation

C[O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][S:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]2[C:16]=1[CH2:17][C:18]1[C:19]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=2[S:21][CH:22]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:27][C:25]1[CH:24]=[CH:23][C:20]2[S:21][CH:22]=[C:18]([CH2:17][C:16]3[N:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]4=[N:9][C:8]=3[S:7][CH2:6][CH2:5][CH2:4][C:3]([OH:28])=[O:2])[C:19]=2[CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 15 mg (0.04 mmol) of 4-[3-(5-chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-ylsulfanyl]-butyric acid methyl ester in 2 mL of THF is treated with a solution of 10 mg (0.24 mmol) of lithium hydroxide monohydrate in 1 mL of water at room temperature. The resulting mixture is heated to 50° C., and stirred at this temperature for 2 h. The reaction mixture is then cooled to room temperature and concentrated in vacuo. The residue is purified by preparative TLC on silica gel to give the title compound. LCMS (ESMS): m/z 417 (M+H+).

Workup

temperatureThe reaction mixture is then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue is purified by preparative TLC on silica gel

Sources & evidence

ORD record: ord-64da4a8a10254bfea743bc6a322bf605
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193214B2

Reaction notes

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