Benzenesulfonamide, 3-nitro- → 4-[4-(3,3-Diphenylprop-2-enyl)piperazin-1-yl]-n-[(3-nitrophenyl)sulfonyl]benzamide

HRID 1968601Notes

Reaction equation

HRID 1968601 reaction equation
[C:1]1([C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:31]([C:34]1[CH:35]=[C:36]([S:40]([NH2:43])(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=1)([O-:33])=[O:32].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[C:1]1([C:7]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([NH:43][S:40]([C:36]4[CH:37]=[CH:38][CH:39]=[C:34]([N+:31]([O-:33])=[O:32])[CH:35]=4)(=[O:42])=[O:41])=[O:21])=[CH:18][CH:17]=3)[CH2:14][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 67138Benzenesulfonamide, 3-nitro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671447144-[4-(3,3-Diphenylprop-2-en-1-yl)piperazin-1-yl]benzoic acid

Product 1

HCID 468425544-[4-(3,3-Diphenylprop-2-enyl)piperazin-1-yl]-n-[(3-nitrophenyl)sulfonyl]benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of EXAMPLE 1D (39.8 mg, 0.05 mmol), 3-nitrobenzenesulfonamide (20.2 mg, 0.05 mmol), 4-dimethylaminopyridine (24.4 mg, 0.1 mmol) and 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (38.4 mg, 0.1 mmol) in dichloromethane (3 ml) was stirred for 16 hours at room temperature. The reaction mixture was concentrated and purified by RP HPLC (Zorbax SB-C8, gradient 30% to 100% CH3CN/water/0.1% TFA). 1H NMR (500 MHz, dimethylsulfoxide-d6) δ 10.49 (br s, 1H), 8.68 (s, 1H), 8.43-8.52 (m, 1H), 8.36 (d, 1H), 7.90 (t, 1H), 7.79 (d, 2H), 7.47 (t, 2H), 7.43 (t, 1H), 7.32-7.40 (m, 3H), 7.27 (d, 2H), 7.18 (d, 2H), 6.99 (d, 2H), 6.26 (t, 1H), 3.84 (d, 2H), 3.38-3.54 (br s, 4H), 3.32 (br s, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by RP HPLC (Zorbax SB-C8, gradient 30% to 100% CH3CN/water/0.1% TFA)

Sources & evidence

ORD record
ord-4f2079ac40064927b0e6f7f63ace7dd9
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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