Piperidine → HCID 69883661, compound

HRID 2120259Notes

Reaction equation

[CH:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][CH2:9][CH2:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][C:14](=[O:20])[NH:15]3)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:23]([CH2:26][CH2:27][C:28]1[C:29]([CH3:36])=[C:30]([CH:34]=O)[NH:31][C:32]=1[CH3:33])([OH:25])=[O:24].N1CCCCC1>C(O)C>[CH:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][CH2:9][CH2:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[C:13](=[CH:34][C:30]2[NH:31][C:32]([CH3:33])=[C:28]([CH2:27][CH2:26][C:23]([OH:25])=[O:24])[C:29]=2[CH3:36])[C:14](=[O:20])[NH:15]3)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-[2-(4-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one (118 mg, 0.4 mmol), 4-carboxyethyl-3,5-dimethyl-2-formylpyrrole (78 mg, 0.4 mmol) and piperidine (0.3 mL) in 1.0 mL of ethanol was heated in a sealed tube at 90° C. for 18 hours and cooled to room temperature. The reaction mixture was concentrated and the residue was dissolved in methylene chloride followed by the addition of diethyl ether. The precipitate was filtered and washed with ethyl acetate to give 110 mg (58%) of 3-(5-{4-[2-(4-isopropyl-phenoxy)-ethyl]-2-oxo-1,2-dihydro-indol-3-ylidenemethyl}-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid (piperidine salt).

Workup

temperaturecooled to room temperature
concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in methylene chloride
additionfollowed by the addition of diethyl ether
filtrationThe precipitate was filtered
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-c4f95d54eb4f4d34aa7fd924648af937
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689806B1

Reaction notes

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