Triethylamine → HCID 86723303, compound

HRID 2366195Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:12]=1[C:13](Cl)=[O:14].C(N(CC)CC)C>O1CCOCC1>[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:12]=1[C:13]([NH:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])=[O:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-chloro-3-fluoropyridin-4-ylamine (293 mg, 2.0 mmol), 2-chloro-6-fluoro-benzoyl chloride (400 mg, 2.07 mmol) and triethylamine (300 μL, 218 mg, 2.15 mmol) in dioxane (6 mL) was heated at 50° C. for 4 hours. After cooling to ambient temperature, triethylamine (60 μL) and 2-chloro-6-fluorobenzoyl chloride (40 μL) were added. The resultant mixture was heated under reflux for a further 2 hours. The reaction mixture was cooled and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with DCM and the resultant solid was triturated in diethyl ether, filtered, and dried to give the desired compound as a white solid (380 mg, 63% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.46 (br s, 1H), 8.27-8.23 (m, 2H), 7.59 (td, J=8.3, 6.2 Hz, 1H), 7.47 (d, J=8.1 Hz, 1H), 7.42-7.37 (m, 1H). LCMS (Method C): RT=3.34 min, m/z: 303 [M+H+].

Workup

temperatureAfter cooling to ambient temperature
temperatureunder reflux for a further 2 hours
temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel flash chromatography
washeluting with DCM
customthe resultant solid was triturated in diethyl ether
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-7188cbc3cb724dbfa0ef1f0ec5d8c659
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697708B2

Reaction notes

Loading…