Hydrochloric Acid → 2-[2-(2-Bromophenyl)-6-quinolyl]-3-cyclohexyl-imidazo[4,5-b]pyridine-6-carboxylic acid

HRID 1788548Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

Compound 477d (0.139 g, 0.25 mmol) was dissolved in MeOH (3 mL) and 2 N aqueous NaOH (1.5 mL) was added. The mixture was stirred at 55° C. for 2 h and then neutralized with 5 N HCl to pH 3 at 0° C. The precipitates formed was collected by filtration and purified by RP HPLC (15% of buffer B to 95% of buffer B) to give the title compound. Yield 96%.

Workup

customThe precipitates formed
filtrationwas collected by filtration
custompurified by RP HPLC (15% of buffer B to 95% of buffer B)

Sources & evidence

ORD record: ord-406fc899bd3d4b099f369f4a79c20782
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511145B2

Reaction notes

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