1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-methoxy-N,2,6-trimethyl-N-[(4-{[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

HRID 469020Notes

Reaction equation

HRID 469020 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=NC2N(O)N=NC=2C=1.[N:46]1([CH2:51][CH:52]2[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]2)[CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C=O)C>[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:55]3[CH2:54][CH2:53][CH:52]([CH2:51][N:46]4[CH2:50][CH2:49][CH2:48][CH2:47]4)[CH2:57][CH2:56]3)=[O:23])[CH:17]=2)(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 167683474-(Pyrrolidin-1-ylmethyl)piperidineHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 583930044-methoxy-N,2,6-trimethyl-N-[(4-{[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to general procedure AG using 5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (60 mg, 0.17 mmol), EDCI (33 mg, 0.17 mmol), HOAt (24 mg, 0.17 mmol and 4-(pyrrolidin-1-ylmethyl)piperidine (28 mg, 0.17 mmol) in DMF (1 mL). The crude product was purified by FCC and then using prep method C.

Workup

  1. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-f0d6ecb5889a4c78b5ce233cf4aa7421
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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