6-Aminoquinoline → HCID 90308938, compound

HRID 2283661Notes

Reaction equation

C(N(C(C)C)CC)(C)C.Cl[C:11]1[N:12]=[C:13]([S:22][CH3:23])[N:14]=[N:15][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[NH2:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]=[CH:30][CH:29]=[CH:28]2>C(#N)C>[CH3:23][S:22][C:13]1[N:14]=[N:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([NH:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)[N:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Diisopropylethylamine (0.53 ml) was added to a solution of ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (234 mg) and 6-aminoquinoline (173 mg) in acetonitrile (3 ml), and the reaction solution was stirred in a microwave reactor at 100° C. for 1 hour. The solvent was evaporated under vacuum, and then the residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain ethyl 3-(methylthio)-5-(quinolin-6-ylamino)-1,2,4-triazine-6-carboxylate as a white solid.

Workup

customThe solvent was evaporated under vacuum
customthe residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record: ord-936e6345dac9450cac32a7a521e03517
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145414B2

Reaction notes

Loading…