Diisopropylethylamine → 8-(2-Chloro-4-fluorophenyl)-N-(1-(2-methylpyridin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 451457Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1.Br[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22]([C:26]4[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=4)[CH2:21][CH2:20]3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 8-(2-chloro-4-fluorophenyl)-N-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (69 mg, 2 mmol), 4-bromo-2-methylpyridine (34 mg, 0.2 mmol) and N,N-diisopropylethylamine (40 mg, 0.3 mmol) in 1,4-dioxane (0.8 mL) was stirred for 30 minutes at 150° C. in the microwave. Purification by chromatography of the reaction mixture (SiO2, heptane:ethyl acetate 1:1 to ethyl acetate:methanol:ammoniumhydroxide 80:18:2 afforded the title compound as yellow semisolid (21 mg, 24%).

Workup

customPurification by chromatography of the reaction mixture (SiO2, heptane:ethyl acetate 1:1 to ethyl acetate:methanol:ammoniumhydroxide 80:18:2

Sources & evidence

ORD record: ord-bcfe2c26be044d3d8003ebc435e10ed5
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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