Hydrochloric Acid → 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazo[4,5-b] pyridine-2-carboxylic acid

HRID 18518Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

175.0 mg (0.46 mmol) 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazo[4,5-b]pyridine-2-carboxylic acid methyl ester were added to a solution of 19.6 mg (0.82 mmol) LiOH in 6 mL THF and 2 mL H2O. The reaction mixture was stirred for 2 h at 60° C., cooled to room temperature and acidified (pH=2) by the addition of a half concentrated HCl-solution. The precipitate was filtered off and washed with water to give pure 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazo[4,5-b] pyridine-2-carboxylic acid as a brown crystalline solid.

Workup

temperaturecooled to room temperature
filtrationThe precipitate was filtered off
washwashed with water

Sources & evidence

ORD record: ord-8d38bda050e945489a5e99864a5074a3
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741341B2

Reaction notes

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