1,2-Dichloroethane → N-{[5-({4-[(6-Chloropyridin-3-yl)methyl]piperazin-1-yl}carbonyl)-1,3,4-oxadiazol-2-yl]methyl}-4-methoxy-N,2,6-trimethylbenzenesulfonamide

HRID 469113Notes

Reaction equation

HRID 469113 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH3:28])[CH2:14][C:15]2[O:16][C:17]([C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[O:21])=[N:18][N:19]=2)(=[O:12])=[O:11])=[C:5]([CH3:29])[CH:4]=1.[Cl:30][C:31]1[N:36]=[CH:35][C:34]([CH:37]=O)=[CH:33][CH:32]=1.ClCCCl>>[Cl:30][C:31]1[N:36]=[CH:35][C:34]([CH2:37][N:25]2[CH2:24][CH2:23][N:22]([C:20]([C:17]3[O:16][C:15]([CH2:14][N:13]([CH3:28])[S:10]([C:6]4[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[CH3:29])(=[O:11])=[O:12])=[N:19][N:18]=3)=[O:21])[CH2:27][CH2:26]2)=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 27640536-Chloropyridine-3-carbaldehydeHCID 583933044-Methoxy-N,2,6-trimethyl-N-{[5-(piperazin-1-ylcarbonyl)-1,3,4-oxadiazol-2-yl]methyl}benzenesulfonamide

Product 1

HCID 46175823N-{[5-({4-[(6-Chloropyridin-3-yl)methyl]piperazin-1-yl}carbonyl)-1,3,4-oxadiazol-2-yl]methyl}-4-methoxy-N,2,6-trimethylbenzenesulfonamide

Procedure

The title compound was prepared according to general procedure CD using 4-methoxy-N,2,6-trimethyl-N-{[5-(piperazin-1-ylcarbonyl)-1,3,4-oxadiazol-2-yl]methyl}benzenesulfonamide (210 mg, 0.50 mmol), 6-chloropyridine-3-carbaldehyde (84 mg, 0.60 mmol), STAB (210 mg, 0.99 mmol) DCE (4.0 mL) and a few 4 Å molecular sieves. The crude product recrystallised from IPA/MeOH/DCM.

Workup

  1. customThe crude product recrystallised from IPA/MeOH/DCM

Sources & evidence

ORD record
ord-924c3813adef46bbab455ffe373b36e6
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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