Citric Acid → 4-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid

HRID 454762Notes

Reaction equation

CO.[OH-].[Na+].[CH3:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([NH:24][C:25]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:32]=2)=[O:26])[CH:12]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[CH3:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:24][C:25]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:32]=2)=[O:26])[CH:12]=1

Participants

Conditions

Temperature: 52.5 °C

Procedure

Methanol (1.5 mL), dioxane (1.5 mL), and a 2 mol/L aqueous solution of sodium hydroxide (0.24 mL) were added the obtained tert-butyl 4-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoate (71 mg), followed by stirring at 50 to 55° C. for 2 hours. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid was added thereto. The solid substance was collected by filtration to obtain 50 mg of 4-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record: ord-66236804cad6403dae165f2f5e8a5155
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492582B2

Reaction notes

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