1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[4-[[[(3,5-Dimethoxyphenyl)methyl]amino]carbonyl]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester

HRID 514595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514595
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][NH2:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:13]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)(O)=[O:14].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.N(CC)(CC)CC>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][NH:12][C:13]([C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]3)=[CH:20][CH:21]=2)=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 27955084-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

Produkt 1

HCID 582583094-[4-[[[(3,5-Dimethoxyphenyl)methyl]amino]carbonyl]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl esterAusbeute 58,24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 3,5-dimethoxybenzenemethanamine (3.34 g, 20 mmol), 4-(4-carboxyphenyl)-1-piperazinecarboxylic acid, 1-(1,1-dimethylethyl) ester (6.13 g, 20 mmol), EDCI (4.2 g, 22 mmol), HOBT (2.97 g, 22 mmol), N(CH2CH3)3 (12 ml) and DCM (80 ml) was stirred overnight at r.t. The solvent was evaporated. The residue was purified by column chromatography (eluent: petroleum ether/EtOAc 2/1). The desired fractions were collected and the solvent was evaporated. Yield: 5.3 g of 4-[4-[[[(3,5-dimethoxyphenyl)methyl]amino]carbonyl]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (58.24% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customThe residue was purified by column chromatography (eluent: petroleum ether/EtOAc 2/1)
  3. customThe desired fractions were collected
  4. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b355df826f084ac085dc1a123f640177
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107946B2

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