5-chloro-2-(piperazine-1-sulfonyl)-1H-indole → 1-(5-Chloroindol-2-ylsulphonyl)-4-[4-(1-imidazolyl)benzoyl]piperazine

HRID 353460

Reaction equation

HRID 353460 reaction equation
Cl.[N:2]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][N:4]=[CH:3]1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([S:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])=[O:27])=[CH:20]2>CC(C)=O>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([S:26]([N:29]1[CH2:34][CH2:33][N:32]([C:11](=[O:13])[C:10]3[CH:9]=[CH:8][C:7]([N:2]4[CH:6]=[CH:5][N:4]=[CH:3]4)=[CH:15][CH:14]=3)[CH2:31][CH2:30]1)(=[O:28])=[O:27])=[CH:20]2

Participants

4

Reactant 2

HCID 227105715-chloro-2-(piperazine-1-sulfonyl)-1H-indoleHCID 43810723HCID 43810723, compound

Product 1

HCID 99343981-(5-Chloroindol-2-ylsulphonyl)-4-[4-(1-imidazolyl)benzoyl]piperazineYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

By an analogous method, starting from 4-(1-imidazolyl)benzoic acid hydrochloride and 1-(5-chloroindol-2-ylsulphonyl)piperazine, was prepared 1-(5-chloroindol-2-ylsulphonyl)-4-[4-(1-imidazolyl)benzoyl]piperazine (375 mg, 60% yield) as colourless crystals from acetone; m.p. 155-165° C., 1H NMR (d6DMSO) 3.0-3.2 ppm (broad s, 4H), 3.4-3.8 ppm (broad s, 4H), 7.0 ppm (s, 1H), 7.1 ppm (s, 1H), 7.3 ppm (dd, 1H), 7.5 ppm (m, 3H), 7.7 ppm (d, 2H), 7.8 ppm (m, 2M), 8.3 ppm (s, 1H), 12.4 ppm (broad s, 1H), the spectrum also contained a signal due to acetone, ca 0.05 mol. eq.; MS (M+H)+ 470/472.

Sources & evidence

ORD record
ord-82bc999cf39849ac8078170352e6c961
Source dataset
uspto-grants-2004_06
Patent number
US06753331B1

Linked notes

Loading…