Nitrogen → HCID 86690320, Verbindung

HRID 1521900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521900
Br[C:2]1[C:3]([NH2:22])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:7]=1.N#N.C(N(CC)CC)C.[C:32]([OH:40])(=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][C:37]#[CH:38]>O1CCOCC1.C(Cl)Cl.[Cu]I.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(Cl)Cl>[NH2:22][C:3]1[C:2]([C:38]#[C:37][CH2:36][CH2:35][CH2:34][CH2:33][C:32]([OH:40])=[O:39])=[N:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:4]=1

Komponenten

9

Edukt 4

HCID 947NitrogenHCID 8471TriethylamineHCID 43779506-Heptynoic acidHCID 86690308HCID 86690308, Verbindung

Produkt 1

HCID 86690320HCID 86690320, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418807HCID 178418807, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3-Bromo-5,6-di-p-tolylpyrazin-2-amine (Example 1, step 3)(200 mg, 0.565 mmol) in anhydrous dioxane (10 ml), degassed with N2 was treated with triethylamine (0.708 ml, 5.08 mmol), hept-6-ynoic acid (0.179 ml, 1.129 mmol), copper(I) iodide (32.3 mg, 0.169 mmol) and PdCl2(dppf)-CH2Cl2-adduct (46.1 mg, 0.056 mmol). The reaction mixture was stirred at room temperature for 16 hours. The resulting mixture was diluted with DCM (10 ml) and dry loaded onto silica. Purification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane followed by 20% MeOH in EtOAc afforded the titled compound;

Aufarbeitung

  1. customdry
  2. customPurification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e89f450387274348b8b774600311f6a3
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073932B2

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