Triethylamine → Methyl 4-[7-(1-quinolin-6-ylethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoate

HRID 500233Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.Cl[CH:19]([CH:22]([C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][CH:28]=[CH:27]2)[CH3:23])[CH:20]=O.C(N(CC)CC)C>C(O)(C)C>[N:30]1[C:31]2[C:26](=[CH:25][C:24]([CH:22]([C:19]3[N:3]4[N:4]=[C:5]([C:8]5[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=5)[CH:6]=[N:7][C:2]4=[N:1][CH:20]=3)[CH3:23])=[CH:33][CH:32]=2)[CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of methyl 4-(3-amino-1,2,4-triazin-6-yl)benzoate (50 mg, 0.217 mmol) and 2-chloro-3-quinolin-6-ylbutanal (61 mg, 0.26 mmol) in isopropyl alcohol (3.0 mL) was heated at 110° C. for 48 h. The mixture was adjusted to pH 9 by adding triethylamine. The volatiles were removed under reduced pressure and the residue was purified by chromatography on silica gel with EtOAc in methylene chloride (0-60%) to afford the desired product (0.020 g, 22%). LCMS: (M+H)=410.0.

Workup

customThe volatiles were removed under reduced pressure
customthe residue was purified by chromatography on silica gel with EtOAc in methylene chloride (0-60%)

Sources & evidence

ORD record: ord-e50457b7725f4613b24bdd83653ab66a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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