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

HRID 571987Notes

Reaction equation

HRID 571987 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][C:12](=[O:20])OC2C=CC=CC=2)=[CH:3][CH:2]=1.[CH3:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=[C:30]([C:36]([F:39])([F:38])[F:37])[N:29]=2)[CH2:24][CH2:23]1.C(N(CC)CC)C>CS(C)=O.O>[CH3:21][CH:22]1[CH2:23][CH2:24][N:25]([C:28]2[C:33]([CH2:34][NH:35][C:12]([NH:11][C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=[CH:2][CH:3]=3)=[O:20])=[CH:32][CH:31]=[C:30]([C:36]([F:39])([F:37])[F:38])[N:29]=2)[CH2:26][CH2:27]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 58873687(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamineHCID 86676323Phenyl quinolin-4-ylcarbamate

Product 1

HCID 712370471-((2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-4-yl)urea

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Phenyl quinolin-4-ylcarbamate (crude 139 mg, 0.53 mmol) and (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (144 mg, 0.53 mmol) were dissolved in dimethyl sulfoxide. Then triethylamine (0.15 mL, 1.06 mmol) was added to it. The mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2301d887842145e9a18c7953c24e5e43
Source dataset
uspto-grants-2015_05
Patent number
US09029378B2

Reaction notes

Loading…