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

HRID 469123Notes

Reaction equation

HRID 469123 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.[CH3:27][N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:30][CH2:29]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:38]3[CH2:37][CH2:36][N:35]([CH2:34][CH:31]4[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]4)[CH2:40][CH2:39]3)=[O:23])[N:17]=2)(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 16682925TrimethylaluminumHCID 58393139Ethyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 461764954-Methoxy-N,2,6-trimethyl-N-{[3-({4-[(1-methylpiperidin-4-yl)methyl]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 (35 mg, 0.09 mmol), 1-[(1-methylpiperidin-4-yl)methyl]piperazine (34 mg, 0.17 mmol) and trimethylaluminium (2 M in toluene, 0.08 mL) in DCE (3 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-c752ad9d7c59411ea38131be1fb23846
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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