1-(2-pyrrolidin-1-ylethyl)piperazine → Ammonia

HRID 469115Notes

Reaction equation

HRID 469115 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[N:20]=[C:19]([C:21]([O:23]CC)=O)[O:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1.[N:27]1([CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:31][CH2:30][CH2:29][CH2:28]1.C[Al](C)C>ClCCCl>[NH3:13].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH3:14])[CH2:15][C:16]2[N:20]=[C:19]([C:21]([N:37]3[CH2:36][CH2:35][N:34]([CH2:33][CH2:32][N:27]4[CH2:28][CH2:29][CH2:30][CH2:31]4)[CH2:39][CH2:38]3)=[O:23])[O:18][N:17]=2)(=[O:11])=[O:12])=[C:5]([CH3:26])[CH:4]=1

Participants

6

Reactant 3

HCID 27372501-(2-pyrrolidin-1-ylethyl)piperazineHCID 16682925TrimethylaluminumHCID 58393145Ethyl 3-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl] (methyl)amino}methyl)-1,2,4-oxadiazole-5-carboxylate

Product 2

HCID 222AmmoniaHCID 46175724HCID 46175724, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared according to general procedure AT using ethyl 3-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,2,4-oxadiazole-5-carboxylate (30 mg, 0.08 mmol), 1-[2-(pyrrolidin-1-yl)ethyl]piperazine (29 mg, 0.16 mmol) and trimethylaluminium (2 M in toluene, 0.08 mL) in DCE (5 mL). The crude product was purified using FCC, eluting with 95:4.5:0.5 DCM:MeOH:NH3, to afford the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified
  3. washeluting with 95:4.5:0.5 DCM

Sources & evidence

ORD record
ord-cfef7b8cc2ec476d9046486b0aede08b
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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