1,1'-Carbonyldiimidazole → 4-methoxy-N,2,6-trimethyl-N-[(4-{[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

HRID 469018Notes

Reaction equation

HRID 469018 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][CH:19]=[C:18]([C:21]([OH:23])=O)[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[N:37]1([CH2:42][CH2:43][N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:41][CH2:40][CH2:39][CH2:38]1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:24])[C:6]([S:10]([N:13]([CH3:14])[CH2:15][C:16]2[O:20][CH:19]=[C:18]([C:21]([N:47]3[CH2:46][CH2:45][N:44]([CH2:43][CH2:42][N:37]4[CH2:38][CH2:39][CH2:40][CH2:41]4)[CH2:49][CH2:48]3)=[O:23])[CH:17]=2)(=[O:12])=[O:11])=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27372501-[2-(Pyrrolidin-1-yl)ethyl]piperazineHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 583930824-methoxy-N,2,6-trimethyl-N-[(4-{[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to general procedure AA using 5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (69 mg, 0.20 mmol), CDI (63 mg, 0.39 mmol) and 1-[2-(pyrrolidin-1-yl)ethyl]piperazine (72 mg, 0.39 mmol) in THF (4 mL). The crude product was purified using prep method A.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-541d3806268b436c87928e731abc37d3
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

Loading…