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

HRID 75938

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-7fe79be0e3314cd9b2c9e39532c9b485
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835465B2

Linked notes

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