1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl}furan-3-carboxamide

HRID 469025Notes

Reaction equation

HRID 469025 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.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:46]1([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][NH2:60])=[CH:54][CH:53]=2)[CH2:50][CH2:49][CH2:48][CH2:47]1>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:60][CH2:59][CH2:58][C:55]3[CH:56]=[CH:57][C:52]([CH2:51][N:46]4[CH2:50][CH2:49][CH2:48][CH2:47]4)=[CH:53][CH:54]=3)=[O:23])[CH:17]=2)[CH3:14])(=[O:11])=[O:12])=[C:5]([CH3:24])[CH:4]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 164950372-[4-(Pyrrolidin-1-ylmethyl)phenyl]ethanamineHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 461761575-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl}furan-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to general procedure AC using 5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (76 mg, 0.22 mmol), EDCI (50 mg, 0.26 mmol), HOBt (35 mg, 0.26 mmol), TEA (0.030 mL, 0.22 mmol) and 2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethanamine (40 mg, 0.20 mmol) in DMF (5 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-ba7812e9308242eab3872910c739e75e
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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