1,1'-Carbonyldiimidazole → 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-[4-(pyrrolidin-1-ylmethyl)benzyl]furan-3-carboxamide

HRID 469016Notes

Reaction equation

HRID 469016 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][C:43]2[CH:48]=[CH:47][C:46]([CH2:49][NH2:50])=[CH:45][CH:44]=2)[CH2:41][CH2:40][CH2:39][CH2:38]1>C1COCC1.CN(C=O)C>[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]([NH:50][CH2:49][C:46]3[CH:45]=[CH:44][C:43]([CH2:42][N:37]4[CH2:41][CH2:40][CH2:39][CH2:38]4)=[CH:48][CH:47]=3)=[O:23])[CH:17]=2)[CH3:14])(=[O:11])=[O:12])=[C:5]([CH3:24])[CH:4]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 49628544-(Pyrrolidin-1-ylmethyl)benzylamineHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 583930735-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-[4-(pyrrolidin-1-ylmethyl)benzyl]furan-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 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 (75 mg, 0.21 mmol), CDI (41 mg, 0.25 mmol) and 1-[4-(pyrrolidin-1-ylmethyl)phenyl]methanamine (37 mg, 0.21 mmol) in THF (4.5 mL) and DMF (0.6 mL). A portion of the crude product was purified using prep method A.

Workup

  1. customA portion of the crude product was purified

Sources & evidence

ORD record
ord-cc037d676b5943cd9caf70903f5d2ec7
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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