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Phenyl 4-(methylsulfonamidomethyl)phenylcarbamate → N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide

HRID 1428711
Notes
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Reaction equation

HRID 1428711 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:22])OC2C=CC=CC=2)=[CH:9][CH:8]=1)(=[O:4])=[O:3].[C:23]1([CH3:41])[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=[C:31]([C:37]([F:40])([F:39])[F:38])[N:30]=2)[CH:24]=1>CN(C)C1C=CN=CC=1>[C:23]1([CH3:41])[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[C:34]([CH2:35][NH:36][C:14](=[O:22])[NH:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:12][CH:11]=3)=[CH:33][CH:32]=[C:31]([C:37]([F:39])([F:38])[F:40])[N:30]=2)[CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 86679364Phenyl 4-(methylsulfonamidomethyl)phenylcarbamateHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 71539427N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
50 °C

Procedure

To a solution of phenyl 4-(methylsulfonamidomethyl)phenylcarbamate (59 mg, 0.18 mmol) acetonitrile (3 mL) was added 4-dimethylaminopyridine (23 mg, 0.18 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (49 mg, 0.18 mmol) at room temperature. The reaction mixture was heated to 50° C. for 16 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. 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 N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide (example 2) (57 mg, 63%).

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  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 to N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide (example 2) (57 mg, 63%)

Sources & evidence

ORD record
ord-826b80af24b242dbbeaa84c6270e1eb7
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937092B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes