Piperidine → 4-(2-carboxyethyl)-3-methyl-5-(6-methoxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid

HRID 24538

Reaction equation

C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=O)=[C:9]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[C:10]=1[CH3:11])=[O:5])C.[CH3:21][O:22][C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][C:28](=[O:32])[NH:29]2)=[CH:25][CH:24]=1.N1CCCCC1.[OH-].[K+]>C(O)C>[C:14]([CH2:13][CH2:12][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:3])=[O:5])[NH:7][C:8]=1[CH:19]=[C:27]1[C:26]2[C:30](=[CH:31][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[NH:29][C:28]1=[O:32])([OH:16])=[O:15]

Participants

Conditions

Temperature: 95 °C

Procedure

5-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (591 mg), 6-methoxy-2-oxindole (333 mg) and piperidine (0.1 mL) in ethanol (4 mL) were stirred at 90° C for 2 hours. Potassium hydroxide (537 mg) was added to the mixture and it was then stirred at 95° C. for and additional hour. The reaction mixture was cooled and concentrated, dissolved in water, and acidified with 2 N hydrochloric acid to pH 2. The precipitate was filtered, washed with water, and dried in a vacuum oven overnight to give 730 mg (99%) of 4-(2-carboxyethyl)-3-methyl-5-(6-methoxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated
dissolutiondissolved in water
filtrationThe precipitate was filtered
washwashed with water
customdried in a vacuum oven overnight

Sources & evidence

ORD record: ord-af289579989748c1aca026cdf56f41e5
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855730B2

Linked notes

Loading…