1-[(Pyridin-3-yl)methyl]piperazine → 4-Methoxy-N,2,6-trimethyl-N-[(3-{[4-(pyridin-3-ylmethyl)piperazin-1-yl]carbonyl}-1,2,4-oxadiazol-5-yl)methyl]benzenesulfonamide

HRID 469124Notes

Reaction equation

HRID 469124 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][N:19]=[C:18]([C:21]([O:23]CC)=O)[N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:28]=1.C[Al](C)C>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:26])[C:6]([S:10]([N:13]([CH3:14])[CH2:15][C:16]2[O:20][N:19]=[C:18]([C:21]([N:37]3[CH2:38][CH2:39][N:34]([CH2:33][C:29]4[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=4)[CH2:35][CH2:36]3)=[O:23])[N:17]=2)(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 1569751-[(Pyridin-3-yl)methyl]piperazineHCID 16682925TrimethylaluminumHCID 58393139Ethyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 461752064-Methoxy-N,2,6-trimethyl-N-[(3-{[4-(pyridin-3-ylmethyl)piperazin-1-yl]carbonyl}-1,2,4-oxadiazol-5-yl)methyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared according to general procedure AT using ethyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,2,4-oxadiazole-3-carboxylate (27 mg, 0.07 mmol), 1-(pyridin-3-ylmethyl)piperazine (40 mg, 0.23 mmol) and trimethylaluminium (2 M in toluene, 0.08 mL) in DCE (2 mL). A portion of the crude product was purified using prep method D.

Workup

  1. customA portion of the crude product was purified

Sources & evidence

ORD record
ord-2ac1081fe7cc410c8a3a7a705d6ec14a
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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