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Methanol → N-[6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-yl]-2-pyridinecarboxamide

HRID 1616002
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1616002
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([NH2:20])[C:13]4[CH:14]=[N:15][N:16]([CH3:19])[C:17]=4[CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN(C(C)C)C(C)C.Cl.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37](Cl)=[O:38].CO>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][N:16]4[CH3:19])=[C:12]([NH:20][C:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=4)=[O:38])[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 582680236-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-amine

Produkt 1

HCID 44540780N-[6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-yl]-2-pyridinecarboxamideAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-amine (70 mg, 0.27 mmol) was dissolved in DCM (3 ml) and treated with DIPEA (0.145 ml). 2-Pyridinecarbonyl chloride hydrochloride (59.5 mg, 0.34 mmol) was added and the reaction was stirred for 5 h. MeOH (2 ml) was added and the reaction stirred overnight. The solvent was evaporated and the residue was treated with DCM/Methanol (1:1, 2 ml) then evaporated to dryness. The product was dissolved in DMSO (2 ml) and purified by Mass Directed Automated Preparative HPLC (Method B). Fractions containing product were combined and dried to give the title compound (23 mg).

Aufarbeitung

  1. stirringthe reaction stirred overnight
  2. customThe solvent was evaporated
  3. additionthe residue was treated with DCM/Methanol (1:1, 2 ml)
  4. customthen evaporated to dryness
  5. dissolutionThe product was dissolved in DMSO (2 ml)
  6. custompurified by Mass Directed Automated Preparative HPLC (Method B)
  7. additionFractions containing product
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3871c9899bb0483b8250bb552bb65e63
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765743B2

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