N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride → N-{4-[3-(4-t-butylbenzyl)ureidomethyl]-2-fluorophenyl}methanesulfonamide

HRID 2423351Notes

Reaction equation

HRID 2423351 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:6][NH2:7].[C:16]([C:20]1[CH:29]=[CH:28][C:23]([CH2:24][N:25]=[C:26]=[O:27])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.ClCCl>[C:16]([C:20]1[CH:29]=[CH:28][C:23]([CH2:24][NH:25][C:26](=[O:27])[NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:3]([F:2])[CH:4]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideHCID 220422271-Tert-butyl-4-(isocyanatomethyl)benzene

Product 1

HCID 11625640N-{4-[3-(4-t-butylbenzyl)ureidomethyl]-2-fluorophenyl}methanesulfonamideYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3-fluoro-4-methanesulfonylaminobenzylamine hydrochloride (1.13 g) prepared in step 3 of Example 1 was dissolved in DMF (6 mL) and diluted with dichloromethane (35 mL). To the solution were added 4-t-butylbenzylisocyanate (1.09 g) and TEA (1.2 mL) and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, diluted with ethylacetate (20 mL) and washed with water and saturated NaCl aqueous solution. The resulting solution was dried over anhydride MgSO4 and the remaining liquid was concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane/ethyl acetate=312) to yield title compound (1.23 g, 53%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethylacetate (20 mL)
  3. washwashed with water and saturated NaCl aqueous solution
  4. dry with materialThe resulting solution was dried over anhydride MgSO4
  5. concentrationthe remaining liquid was concentrated under reduced pressure
  6. customThe residue was purified with column chromatography (n-hexane/ethyl acetate=312)

Sources & evidence

ORD record
ord-4a5af75ab30f48909c6e26acbf18f74a
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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