(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine → N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamide

HRID 1428768Notes

Reaction equation

HRID 1428768 reaction equation
[CH2:1]([S:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:23])OC2C=CC=CC=2)=[CH:10][CH:9]=1)(=[O:5])=[O:4])[CH3:2].[C:24]1([CH3:42])[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=[C:32]([C:38]([F:41])([F:40])[F:39])[N:31]=2)[CH:25]=1>C(#N)C.CN(C)C1C=CN=CC=1>[C:24]1([CH3:42])[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[C:35]([CH2:36][NH:37][C:15](=[O:23])[NH:14][C:11]3[CH:10]=[CH:9][C:8]([CH2:7][NH:6][S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:13][CH:12]=3)=[CH:34][CH:33]=[C:32]([C:38]([F:40])([F:39])[F:41])[N:31]=2)[CH:25]=1

Participants

5

Reactant 2

HCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamineHCID 86680222Phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate

Product 1

HCID 71539386N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamideYield 45%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate (74 mg, 0.22 mmol) in acetonitrile (3 mL) was added 4-dimethylaminopyridine (27 mg, 0.22 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (59 mg, 0.22 mmol) at room temperature. The reaction mixture was heated to 50° C. for 15 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamide (example 82) (50 mg, 45%).

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethylacetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-76637c4f762f45209e8f181ff608d86d
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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