Pyridine → HCID 22713764, compound

HRID 352159Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([OH:10])=O)[CH2:3]1.C(Cl)(=O)C(Cl)=O.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[NH2:22].N1C=CC=CC=1>ClCCl>[CH3:29][O:28][C:24]1[CH:23]=[C:21]([NH:22][C:8](=[O:10])[CH2:7][CH:4]2[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]2)[CH:20]=[C:19]([O:18][CH3:17])[C:25]=1[O:26][CH3:27]

Participants

Conditions

Temperature: 2.5 °C

Procedure

To a solution of 1.0 g (7 mmol) of 3-oxocyclopentyl acetic acid in dichloromethane (18 mL) and DMP (1 mL), was added 0.68 mL (7.7 mmol) oxalyl chloride. After 30 min, the solvent was removed in vacuo. The residue was dissolved in dichloromethane (20 mL), cooled to 0-5° C., and 1.29 g of 3,4,5-trimethoxyaniline (0.63 mmol) was added followed by 0.68 mL of pyridine (8.4 mmol). After 15 min, the reaction was allowed to warm to ambient temperature. After 2 h, the reaction was rinsed with 1N HCl, followed by aq. sodium bicarbonate, and water (3×). The organic layer was dried, the solvent removed in vacuo and the residue chromatographed on a silica gel with 2% methanol in methylene chloride to yield 0.25 g of the title compound. MS(ES+)m/z=308.

Workup

customthe solvent was removed in vacuo
dissolutionThe residue was dissolved in dichloromethane (20 mL)
waitAfter 15 min
temperatureto warm to ambient temperature
waitAfter 2 h
washthe reaction was rinsed with 1N HCl
customThe organic layer was dried
customthe solvent removed in vacuo
customthe residue chromatographed on a silica gel with 2% methanol in methylene chloride

Sources & evidence

ORD record: ord-f547dfe0b7ea41f6abce8a654b99369d
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743794B2

Reaction notes

Loading…