Triethylamine → 2-Chloro-5-fluoro-6-(5-isopropoxy-1H-pyrazol-3-ylamino)nicotinonitrile

HRID 75919

Reaction equation

[CH:1]([O:4][C:5]1[NH:9][N:8]=[C:7]([NH2:10])[CH:6]=1)([CH3:3])[CH3:2].[Cl:11][C:12]1[N:19]=[C:18](Cl)[C:17]([F:21])=[CH:16][C:13]=1[C:14]#[N:15].C(N(CC)CC)C>C1COCC1>[Cl:11][C:12]1[N:19]=[C:18]([NH:10][C:7]2[CH:6]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[NH:9][N:8]=2)[C:17]([F:21])=[CH:16][C:13]=1[C:14]#[N:15]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 5-isopropoxy-1H-pyrazol-3-amine (0.96 g, 6.8 mmol), 2,6-dichloro-5-fluoronicotinonitrile (1.3 g, 6.8 mmol), and triethylamine (0.9 g, 8.8 mmol) in THF (30 ml) was heated to 60° C. for 4 days, and then cooled to 25° C., at which point the product precipitated. The resulting solid was filtered and washed with hexanes (100 ml) to give the title compound (1.0 g, 50%). MS: Calcd.: 295. Found: [M+H]+ 296.

Workup

customprecipitated
filtrationThe resulting solid was filtered
washwashed with hexanes (100 ml)

Sources & evidence

ORD record: ord-ea0f5851f4bf47c38c818123b68e1492
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835465B2

Linked notes

Loading…