Diisopropylethylamine → HCID 58397933, compound

HRID 451581Notes

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.Cl[C:29]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31][N:30]=1.C(N(CC)C(C)C)(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[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31][N:30]=2)[CH2:3]1

Participants

Conditions

Temperature: 150 °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 (75 mg, 196 μmol), 4-chloro-6-methylpyrimidine (27.7 mg, 215 μmol) and N,N-diisopropylethylamine (37.9 mg, 49.9 μL, 293 μmol) in dioxane (4 mL) was heated to 150° C. in the microwave for 1 hour. Further 4-chloro-6-methylpyrimidine (27.7 mg, 215 μmol) and N,N-diisopropylethylamine (37.9 mg, 49.9 μL, 293 μmol) were added and heated to 150° C. in the microwave for another hour. Further 4-chloro-6-methylpyrimidine (27.7 mg, 215 μmol) and N,N-diisopropylethylamine (37.9 mg, 49.9 μL, 293 μmol) were added and heated to 110° C. for 12 hours. The crude material was directly purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane). The title compound was obtained as light yellow foam (25 mg, 22%). MS ISP (m/e): 476.1 (100) [(M+H)+].

Workup

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

Sources & evidence

ORD record: ord-5dfd6a75d0ee4efb990ec3a682c5beb0
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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