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

HRID 500219Notes

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]([C:22]1([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)[CH2:24][CH2:23]1)[CH:20]=O.C(N(CC)CC)C>C(O)(C)C>[N:31]1[C:32]2[C:27](=[CH:26][C:25]([C:22]3([C:19]4[N:3]5[N:4]=[C:5]([C:8]6[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=6)[CH:6]=[N:7][C:2]5=[N:1][CH:20]=4)[CH2:24][CH2:23]3)=[CH:34][CH:33]=2)[CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of methyl 4-(3-amino-1,2,4-triazin-6-yl)benzoate (160 mg, 0.70 mmol) and chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde (200 mg, 0.83 mmol) in isopropyl alcohol (6 mL) was heated at 110° C. for 24 h. The mixture was adjusted to pH 9 by adding triethylamine and then the volatiles were removed under reduced pressure. The residue was purified by chromatography on silica gel with EtOAc in CH2Cl2 (0-60%) to afford the desired product (130 mg, 44%). LCMS: (M+H)=421.1.

Workup

customthe volatiles were removed under reduced pressure
customThe residue was purified by chromatography on silica gel with EtOAc in CH2Cl2 (0-60%)

Sources & evidence

ORD record: ord-9dfa0fd01c3a44bdab09e85e9f88fa4e
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

Loading…