Water → HCID 86594554, Verbindung

HRID 1744059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744059
Br[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C@@H:8]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([NH:11][CH2:12][C:13]#[N:14])=[O:10])=[CH:4][CH:3]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:13]([CH2:12][NH:11][C:9]([C@@H:8]([NH:7][CH2:6][C:5]1[CH:19]=[CH:20][C:2]([C:37]2[CH:36]=[CH:35][C:34]([N:31]3[CH2:30][CH2:29][N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[CH2:33][CH2:32]3)=[CH:39][CH:38]=2)=[CH:3][CH:4]=1)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:10])#[N:14]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 52330144-(4-BOC-Piperazino)phenylboronic acidHCID 44403029HCID 44403029, Verbindung

Produkt 1

HCID 86594554HCID 86594554, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To (2S)-2-[(4-bromobenzyl)amino]-N-(cyanomethyl)-4-methylpentanamide (285 mg, 0.843 mmol) and 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (315 mg, 1.02 mmol) in DMF (10 mL) under dry nitrogen was added aqueous sodium carbonate (2 M, 1.3 mL, 2.53 mmol) followed by the catalyst PdCl2(dppf) (25 mg, 0.026 mmol). The reaction was heated to 95° C. for 0.5 hours and more PdCl2(dppf) (25 mg, 0.026 mmol) was added and the reaction mixture was heated overnight. Water was added and the product extracted with ether (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6) to afford tert-butyl 4-(4′-{[((1S)-1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)amino]methyl}[1,1′-biphenyl]-4-yl)-1-piperazinecarboxylate.

Aufarbeitung

  1. temperaturethe reaction mixture was heated overnight
  2. extractionthe product extracted with ether (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography over silica gel (EtOAc/Hex, 4/6)

Quellen und Nachweise

ORD-Eintrag
ord-4fac6f9dacb34f3ba119454af9ca403c
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012075B2

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