Water → n-{2-{[(4,4-Difluorocyclohexyl)methyl]amino}-5-[(ethylsulfonyl)amino]phenyl}-2,2-dimethylpropanamide

HRID 1987226Notes

Reaction equation

HRID 1987226 reaction equation
[C:1]([C:5](Cl)=[O:6])([CH3:4])([CH3:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11]([NH:25][S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])[CH:12]=[CH:13][C:14]=1[NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][C:20]([F:24])([F:23])[CH2:19][CH2:18]1.CCN(CC)CC.O>C(Cl)Cl>[F:24][C:20]1([F:23])[CH2:21][CH2:22][CH:17]([CH2:16][NH:15][C:14]2[CH:13]=[CH:12][C:11]([NH:25][S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[CH:10][C:9]=2[NH:8][C:5](=[O:6])[C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 11559310N-(3-amino-4-{[(4,4-difluorocyclohexyl)methyl]amino}phenyl)ethanesulfonamide

Product 1

HCID 11654905n-{2-{[(4,4-Difluorocyclohexyl)methyl]amino}-5-[(ethylsulfonyl)amino]phenyl}-2,2-dimethylpropanamideYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of t-BuCOCl (7.6 g, 0.063 mol) in DCM (150 mL) was slowly added to a solution of N-(3-amino-4-{[(4,4-difluorocyclohexyl)methyl]amino}phenyl)ethanesulfonamide (22 g, 0.063 mol) and Et3N (9.7 mL, 0.069 mol) in DCM (500 mL) at 0° C. The reaction mixture was stirred for 3 hrs. at 0° C. DCM (300 mL) and water (200 mL) were added. The organic layer was separated and washed with water (3×200 mL), brine and dried over anhydrous Na2SO4. The solvent was removed and the crude product was purified on silica gel by flash chromatography (EtOAc:hexane 1:1) to provide the title product (23.3 g) as beige solid.

Workup

  1. customat 0° C
  2. customThe organic layer was separated
  3. washwashed with water (3×200 mL), brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed
  6. customthe crude product was purified on silica gel by flash chromatography (EtOAc:hexane 1:1)

Sources & evidence

ORD record
ord-3853ce08d06e468daed18f21acef6ec5
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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