4-Chloro-n-((4'-fluoro(1,1'-biphenyl)-4-yl)carbonyl)-3-nitrobenzenesulfonamide → 4-((2,2-Dimethylcyclopentyl)amino)-n-((4'-fluoro(1,1'-biphenyl)-4-yl)carbonyl)-3-nitrobenzenesulfonamide

HRID 1785740Notes

Reaction equation

HRID 1785740 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28].[CH3:30][C:31]1([CH3:37])[CH2:35][CH2:34][CH2:33][CH:32]1[NH2:36]>CN(C=O)C>[CH3:30][C:31]1([CH3:37])[CH2:35][CH2:34][CH2:33][CH:32]1[NH:36][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 102249074-Chloro-n-((4'-fluoro(1,1'-biphenyl)-4-yl)carbonyl)-3-nitrobenzenesulfonamideHCID 151965322,2-Dimethylcyclopentan-1-amine

Product 1

HCID 99143314-((2,2-Dimethylcyclopentyl)amino)-n-((4'-fluoro(1,1'-biphenyl)-4-yl)carbonyl)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 1D (50 mg, 0.12 mmol) and 2,2-dimethylcyclopentylamine (65 mg, 0.58 mmol) in DMF (2.0 mL) was heated to 120° C. in a sealed vial with shaking for 16 hours. The mixture was concentrated, dissolved in 1:1/DMSO:methanol (1.0 mL) and purified by reverse phase preparative HPLC using 0.1% TFA in H2O/CH3CN to provide the desired product. MS (APCI(+)) m/e 529 (M+NH4)+; 1H NMR (500 MHz, DMSO-d6) δ 12.45 (br s, 1H), 8.69 (d, 1H), 8.49 (d, 1H), 7.99 (dd, 1H), 7.97 (d, 2H), 7.80 (2d, 4H), 7.39 (d, 1H), 7.33 (t, 2H), 3.88 (ddd, 1H), 2.28-2.25 (m, 1H), 1.75-1.55 (m, 5H), 1.07 (s, 3H), 1.02 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in 1:1/DMSO
  3. custommethanol (1.0 mL) and purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-a5808aaa533c46389a4cf811ce159d0e
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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