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

HRID 571984Notes

Reaction equation

HRID 571984 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:11][C:12](=[O:20])OC1C=CC=CC=1.[CH:21]1([S:27][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)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C>CS(C)=O.O>[CH:21]1([S:27][C:28]2[C:33]([CH2:34][NH:35][C:12]([NH:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[O:20])=[CH:32][CH:31]=[C:30]([C:36]([F:38])([F:39])[F:37])[N:29]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 54327762Phenyl quinolin-2-ylcarbamateHCID 67300770(2-(Cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 712374831-((2-(Cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-2-yl)ureaYield 53%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Phenyl quinolin-2-ylcarbamate (A) (60 mg, 0.23 mmol) and (2-(cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methanamine (69 mg, 0.24 mmol) was dissolved in dimethyl sulfoxide. Then triethylamine (0.06 mL, 0.45 mmol) was added. 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. The crude was purified by column chromatography to give 1-((2-(cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(quinolin-2-yl)urea (example compound II) (55 mg, 53%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-0b0414f8a9864d828224a82ea0e59a43
Source dataset
uspto-grants-2015_05
Patent number
US09029378B2

Reaction notes

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