Pyridine → HCID 66643222, compound

HRID 536713Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][C:21]=1[C:22](Cl)=[O:23].N1C=CC=CC=1>O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:22](=[O:23])[C:21]2[CH:25]=[C:26]([C:29]([F:30])([F:31])[F:32])[CH:27]=[CH:28][C:20]=2[F:19])[N:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of Example 30A (0.7 g, 2.6 mmol) in tetrahydrofuran (20 mL) were added 2-fluoro-5-(trifluoromethyl)benzoyl chloride (0.46 mL, 3.1 mmol, Aldrich) and pyridine (0.62 mL, 7.6 mmol). After stirring at 60° C. for 16 h, the reaction mixture was cooled and quenched with saturated NaHCO3 (20 mL). The aqueous layer was extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, O-25% ethyl acetate in methylene chloride) to afford 0.75 g (67%) of the title compound. MS (ESI+) m/z 438 (M+H)+.

Workup

temperaturethe reaction mixture was cooled
customquenched with saturated NaHCO3 (20 mL)
extractionThe aqueous layer was extracted with ethyl acetate (3×30 mL)
dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-9f2171c5aca6428887e9e251104ddbda
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859596B2

Reaction notes

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