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

HRID 469093Notes

Reaction equation

HRID 469093 reaction equation
[CH:1]1([N:4]([CH2:18][C:19]2[O:23][C:22]([C:24](OCC)=[O:25])=[N:21][N:20]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH3:29][N:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:32][CH2:31]1.C[Al](C)C>ClCCCl>[CH:1]1([N:4]([CH2:18][C:19]2[O:23][C:22]([C:24]([N:39]3[CH2:38][CH2:37][N:36]([CH:33]4[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]4)[CH2:41][CH2:40]3)=[O:25])=[N:21][N:20]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:6])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 16682925TrimethylaluminumHCID 58393194Ethyl 5-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 58393238N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-[(5-{[4-(1-methylpiperidin-4-yl)piperazin-1-yl]carbonyl}-1,3,4-oxadiazol-2-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-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3,4-oxadiazole-2-carboxylate (30 mg, 0.07 mmol), 1-(1-methylpiperidin-4-yl)piperazine (26 mg, 0.14 mmol) and trimethylaluminium (2 M in toluene, 0.07 mL) in DCE (5 mL). A portion of the crude product was purified using FCC, eluting with 95:4.5:0.5 DCM:MeOH:NH3.

Workup

  1. customA portion of the crude product was purified
  2. washeluting with 95:4.5:0.5 DCM

Sources & evidence

ORD record
ord-a146dada81fa4ecbbb4989b57eadf7ce
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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