1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(pyrrolidin-1-ylmethyl)benzyl]furan-3-carboxamide

HRID 469005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469005
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([N:12]([CH2:14][C:15]2[O:19][CH:18]=[C:17]([C:20]([OH:22])=O)[CH:16]=2)[CH3:13])(=[O:11])=[O:10])=[C:4]([Cl:23])[CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:45]1([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([CH2:57][NH2:58])=[CH:53][CH:52]=2)[CH2:49][CH2:48][CH2:47][CH2:46]1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([N:12]([CH2:14][C:15]2[O:19][CH:18]=[C:17]([C:20]([NH:58][CH2:57][C:54]3[CH:53]=[CH:52][C:51]([CH2:50][N:45]4[CH2:49][CH2:48][CH2:47][CH2:46]4)=[CH:56][CH:55]=3)=[O:22])[CH:16]=2)[CH3:13])(=[O:11])=[O:10])=[C:4]([Cl:23])[CH:3]=1

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 49628544-(Pyrrolidin-1-ylmethyl)benzylamineHCID 583934255-({[(4-Bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Produkt 1

HCID 461752845-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(pyrrolidin-1-ylmethyl)benzyl]furan-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (40 mg, 0.09 mmol), EDCI (23 mg, 0.12 mmol) and HOBt (15 mg, 0.11 mmol) in DMF (3 mL) was added 1-[4-(pyrrolidin-1-ylmethyl)phenyl]methanamine (17 mg, 0.09 mmol). The reaction was stirred at ambient temperature for 3 days, then absorbed on to an Isolute SCX-2 cartridge, washing with MeOH and eluting the product with 7M NH3 in MeOH. The filtrate was concentrated in vacuo and a portion of the crude product purified using prep method C.

Aufarbeitung

  1. customabsorbed on to an Isolute SCX-2 cartridge
  2. washwashing with MeOH
  3. washeluting the product with 7M NH3 in MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customa portion of the crude product purified

Quellen und Nachweise

ORD-Eintrag
ord-324fba865f1c4e49bc7aa907919aba5a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623859B2

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