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

HRID 468981Notes

Reaction equation

HRID 468981 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](O)=[O:22])[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.[CH3:37][N:38]1[CH2:43][CH2:42][CH:41]([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:40][CH2:39]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]([CH:41]4[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]4)[CH2:49][CH2:48]3)=[O:22])[CH:17]=2)(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 446319404-Methoxy-N,2,6-trimethyl-N-[(4-{[4-(1-methylpiperidin-4-yl)piperazin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (74 mg, 0.21 mmol) is dissolved in THF (4 mL) and CDI (68 mg, 0.42 mmol) added. The resulting solution was stirred for 90 min prior to the addition of 1-(1-methylpiperidin-4-yl)piperazine (77 mg, 0.42 mmol). The reaction was stirred at ambient temperature for 18 h, concentrated in vacuo and a portion of the resulting crude product purified using prep method B to afford the title compound.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 18 h
  2. concentrationconcentrated in vacuo
  3. customa portion of the resulting crude product purified

Sources & evidence

ORD record
ord-2e50d99e96434e919186a696bd3aa6d2
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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