4-tert-Butylbenzylamine → N-(4-t-butylbenzyl) 3-(3-fluoro-4-methanesulfonylaminophenyl)propionamide

HRID 656303

Reaction equation

HRID 656303 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]([O:17]C)=O)[CH:5]=[CH:6][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[C:19]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1>[C:19]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][NH:28][C:15](=[O:17])[CH2:14][CH2:13][C:4]2[CH:5]=[CH:6][C:7]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[C:2]([F:1])[CH:3]=2)=[CH:29][CH:30]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 27356554-tert-ButylbenzylamineHCID 59684482Methyl 3-(3-fluoro-4-methanesulfonylaminophenyl)propionate

Product 1

HCID 44574279N-(4-t-butylbenzyl) 3-(3-fluoro-4-methanesulfonylaminophenyl)propionamideYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound 26-2 (30 mg) prepared in Step 2 was dissolved in toluene (4 ml) and to the solution was added 4-t-butylbenzylamine (150 μl), followed by refluxing for 3 hours. The resulting mixture was concentrated under reduced pressure and the obtained residue was chromatographed on silica gel column (ethyl acetate/hexane=1/1) to yield the compound 26-3 (28 mg, 58%).

Workup

  1. temperatureby refluxing for 3 hours
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. customthe obtained residue was chromatographed on silica gel column (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-81ad59e9b2904ed59f21a8a1c88c02df
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Linked notes

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