1,2-Dichloroethane → 4-Methoxy-N,2,6-trimethyl-N-{[5-({4-[(1-methyl-1H-imidazol-5-yl)methyl]piperazin-1-yl}carbonyl)-1,3,4-oxadiazol-2-yl]methyl}benzenesulfonamide

HRID 469109Notes

Reaction equation

HRID 469109 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.[CH3:30][N:31]1[C:35]([CH:36]=O)=[CH:34][N:33]=[CH:32]1.ClCCCl>>[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[CH2:23][CH2:24][N:25]([CH2:36][C:35]4[N:31]([CH3:30])[CH:32]=[N:33][CH:34]=4)[CH2:26][CH2:27]3)=[O:21])=[N:18][N:19]=2)(=[O:11])=[O:12])=[C:5]([CH3:29])[CH:4]=1

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 5735921-methyl-1H-imidazole-5-carbaldehydeHCID 583933044-Methoxy-N,2,6-trimethyl-N-{[5-(piperazin-1-ylcarbonyl)-1,3,4-oxadiazol-2-yl]methyl}benzenesulfonamide

Product 1

HCID 673294164-Methoxy-N,2,6-trimethyl-N-{[5-({4-[(1-methyl-1H-imidazol-5-yl)methyl]piperazin-1-yl}carbonyl)-1,3,4-oxadiazol-2-yl]methyl}benzenesulfonamide

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 (42 mg, 0.10 mmol), 1-methyl-1H-imidazole-5-carbaldehyde (13 mg, 0.12 mmol), STAB (42 mg, 0.2 mmol) DCE (0.8 mL) and a few 4 Å molecular sieves. The crude product was purified using prep method D.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-a1b446d4b1464b86b58c176d79568a8b
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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