3-Aminoquinoline → 1-((2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-3-yl)urea

HRID 571985Notes

Reaction equation

HRID 571985 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].NC1C=N[C:17]2[C:22](C=1)=[CH:21][CH:20]=[CH:19][CH:18]=2.[CH3:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]2C(CN)=[CH:35][CH:34]=[C:33]([C:39]([F:42])([F:41])[F:40])[N:32]=2)[CH2:27][CH2:26]1>C(Cl)Cl>[CH3:24][CH:25]1[CH2:26][CH2:27][N:28]([C:31]2[C:11]([CH2:12][NH:8][C:1]([NH:3][C:7]3[CH:6]=[N:5][C:4]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:22][CH:21]=4)=[O:2])=[CH:35][CH:34]=[C:33]([C:39]([F:40])([F:41])[F:42])[N:32]=2)[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 113753-AminoquinolineHCID 682631,1'-CarbonyldiimidazoleHCID 58873687(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 712372131-((2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-3-yl)ureaYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (CU) (1.1 eq.) was added to 3-aminoquinoline (1 eq.) dissolved in methylene chloride. The mixture was stirred during 12 h at room temperature. After that (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (0.98 eq.) was added to the mixture. After 12 h the solvent was evaporated and the mixture was purified by column chromatography (silica gel: 100-200; eluent: 50% ethyl acetate in n-hexane) and give the desired 1-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-3-yl)urea (example compound 12) (100 mg, 42%).

Workup

  1. customAfter 12 h the solvent was evaporated
  2. customthe mixture was purified by column chromatography (silica gel: 100-200; eluent: 50% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-a7d0454ff2be44b3a731740fc35597db
Source dataset
uspto-grants-2015_05
Patent number
US09029378B2

Reaction notes

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