Diisopropylethylamine → HCID 58397871, compound

HRID 451582Notes

Reaction equation

[F:1][C:2]1([F:27])[CH:7]([NH:8][C:9]2[N:26]=[C:12]3[C:13]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[C:18]=4[F:25])=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH2:6][CH2:5][NH:4][CH2:3]1.Br[C:29]1[O:30][C:31]([CH3:34])=[N:32][N:33]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[F:27][C:2]1([F:1])[CH:7]([NH:8][C:9]2[N:26]=[C:12]3[C:13]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[C:18]=4[F:25])=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH2:6][CH2:5][N:4]([C:29]2[O:30][C:31]([CH3:34])=[N:32][N:33]=2)[CH2:3]1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of N-(3,3-difluoropiperidin-4-yl)-8-(2,3,4-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (see example 275b, 75 mg, 196 μmol), 2-bromo-5-methyl-1,3,4-oxadiazole (41.5 mg, 254 μmol) and diisopropylethylamine (50.6 mg, 68.3 μL, 391 μmol) dissolved in dry dioxane (4 mL) was stirred at 110° C. for 3 hours. Further diisopropylethylamine (50.6 mg, 68.3 μL, 391 μmol) and 2-bromo-5-methyl-1,3,4-oxadiazole (41.5 mg, 254 μmol) were added and heated to 110° C. for 12 hours. The solvent was evaporated and the residue was purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane). The title compound was as white foam (36 mg, 40%).

Workup

temperatureheated to 110° C. for 12 hours
customThe solvent was evaporated
customthe residue was purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane)

Sources & evidence

ORD record: ord-48cb0ab95ac24b548d0b080f5fe5fcb9
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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