Benzenesulfonyl chloride → 4''-Trifluoromethyl-biphenyl-2-carboxylic acid (2-benzenesulfonylamino-indan-5-yl)-amide

HRID 1531271Notes

Reaction equation

HRID 1531271 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:8]=2)[CH2:3]1.C(N(C(C)C)CC)(C)C.[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(OCC)(=O)C>C(Cl)Cl>[C:39]1([S:45]([NH:1][CH:2]2[CH2:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([NH:11][C:12]([C:14]4[C:15]([C:20]5[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=5)=[CH:16][CH:17]=[CH:18][CH:19]=4)=[O:13])[CH:8]=3)[CH2:3]2)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 212533824'-Trifluoromethylbiphenyl-2-carboxylic acid (2-amino-indan-5-yl)-amide

Product 1

HCID 98933624''-Trifluoromethyl-biphenyl-2-carboxylic acid (2-benzenesulfonylamino-indan-5-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title F compound (4′-trifluoromethylbiphenyl-2-carboxylic acid (2-amino-indan-5-yl)-amide, 0.100 g, 0.250 mmol) in methylene chloride (10 mL) is added diisopropylethyl amine (0.036 g, 0.280 mmol) followed by benzenesulfonyl chloride (0.046 g, 0.260 mmol). After 1 h, the reaction mixture is poured into ethyl acetate and washed with 1 N HCl, 8% NaHCO3 solution, water, and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give an oil which is purified by silica gel chromatography. Drying under vacuum at 60° C. gives 4′-trifluoromethyl-biphenyl-2-carboxylic acid (2-benzenesulfonylamino-indan-5-yl)-amide as a non-crystalline solid; mp 96° C. sinters. MS (ES+), m/z 537 (M+1), 554 (M+NH4+).

Workup

  1. washwashed with 1 N HCl, 8% NaHCO3 solution, water, and brine
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil which
  5. customis purified by silica gel chromatography
  6. customDrying under vacuum at 60° C.

Sources & evidence

ORD record
ord-bf452675d8a14fada8533b2cacb0e8d9
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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