Triethylamine → 2-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-4-iodonicotinonitrile

HRID 2189898Notes

Reaction equation

[Cl:1][C:2]1[N:9]=[C:8](Cl)[C:7]([F:11])=[C:6]([I:12])[C:3]=1[C:4]#[N:5].CCN(CC)CC.[CH:20]1([C:23]2[NH:27][N:26]=[C:25]([NH2:28])[CH:24]=2)[CH2:22][CH2:21]1>C(#N)C>[Cl:1][C:2]1[N:9]=[C:8]([NH:28][C:25]2[CH:24]=[C:23]([CH:20]3[CH2:22][CH2:21]3)[NH:27][N:26]=2)[C:7]([F:11])=[C:6]([I:12])[C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 80 °C

Procedure

The crude 2,6-dichloro-5-fluoro-4-iodonicotinonitrile (8.0 g, 25.2 mmol), Et3N (3.3 g, 32.8 mmol) and 5-cyclopropyl-1H-pyrazol-3-amine (3.1 g, 25.2 mmol) were placed in ACN (50 ml) and the resulting solution was heated to 80° C. for 24 hours. The reaction was cooled to room temperature, filtered, and the resulting solid was washed with cold ACN, dried, and collected to give the title compound (3.0 g, 29%). MS: Calcd.: 403. Found: [M+H]+ 404.

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered
washthe resulting solid was washed with cold ACN
customdried
customcollected

Sources & evidence

ORD record: ord-233d6bc23b484963b2d8fe90ce3354cd
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324252B2

Reaction notes

Loading…