Triethylamine → 2-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoronicotinonitrile

HRID 1437433Notes

Reaction equation

[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH2:9])[CH:5]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[N:18]=[C:17](Cl)[C:16]([F:20])=[CH:15][C:12]=1[C:13]#[N:14].C(N(CC)CC)C>CC#N>[Cl:10][C:11]1[N:18]=[C:17]([NH:9][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:8][N:7]=2)[C:16]([F:20])=[CH:15][C:12]=1[C:13]#[N:14]

Participants

Conditions

Temperature: 82 °C

Procedure

A solution of 5-cyclopropyl-1H-pyrazol-3-amine (1.9 g, 16.0 mmol) in CH3CN (20 ml) was added dropwise to a solution of 2,6-dichloro-5-fluoronicotinonitrile (3.0 g, 16.0 mmol) and triethylamine (2.1 g, 20.0 mmol) in CH3CN (80 ml) at 25° C. The resulting solution was heated to 82° C. for 18 hrs, and then cooled to 25° C. The resulted precipitate was collected by filtration and washed with CH3CN (100 ml) to give the title compound (3.2 g, 73%). MS: Calcd.: 277. Found: [M+H]+ 278.

Workup

temperaturecooled to 25° C
filtrationThe resulted precipitate was collected by filtration
washwashed with CH3CN (100 ml)

Sources & evidence

ORD record: ord-707d3b91a36a43e8900144508b46ad83
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622482B2

Reaction notes

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