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m-Chloroperbenzoic acid → 1-[5-Isopropyl-4-(1H-pyrrolo[2,3-b]pyridin-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-6-yloxy]-propan-2-ol

HRID 1064253
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1064253
[CH:1]([C:4]1[C:5]([O:15][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:6][N:7]2[C:12]=1[C:11](SC)=[N:10][CH:9]=[N:8]2)([CH3:3])[CH3:2].C([Si](C(C)C)(C(C)C)[N:24]1[C:28]2=[N:29][CH:30]=[C:31]([NH2:33])[CH:32]=[C:27]2[CH:26]=[CH:25]1)(C)C.ClC1C=CC=C(C(OO)=O)C=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)(Cl)Cl.C1COCC1>[CH:1]([C:4]1[C:5]([O:15][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:6][N:7]2[C:12]=1[C:11]([NH:33][C:31]1[CH:32]=[C:27]3[CH:26]=[CH:25][NH:24][C:28]3=[N:29][CH:30]=1)=[N:10][CH:9]=[N:8]2)([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 70297m-Chloroperbenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 222736141H-Pyrrolo[2,3-B]pyridin-5-amine, 1-[tris(1-methylethyl)silyl]-HCID 222736261-(5-Isopropyl-4-methylsulfanylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-propan-2-ol

Produkt 1

HCID 222736641-[5-Isopropyl-4-(1H-pyrrolo[2,3-b]pyridin-5-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-6-yloxy]-propan-2-ol
Ausbeute 1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

1-(5-Isopropyl-4-methylsulfanylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)-propan-2-ol (262 mg, 0.93 mmol, obtained from Example 25 using procedure in Step B of Example 7) and 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-ylamine (290 mg, 0.93 mmol) were dissolved in chloroform and m-chloroperbenzoic acid (60%, 535 mg, 1.86 mmol) was added. The mixture was heated at 120° C. for 10 min in a Personal Chemistry Smith Enrys Optimizer™ microwave oven. The solution was evaporated in vacuo and the residue was purified by preparative HPLC. The isolated product was dissolved in of THF (10 mL) and TBAF (1.0 M, 0.2 mL, 0.2 mmol) was added. The mixture was stirred for 5 min. and the solvent was evaporated in vacuo. The residue was purified by preparative HPLC to afford the title compound (3 mg, 1%).

Aufarbeitung

  1. customThe solution was evaporated in vacuo
  2. customthe residue was purified by preparative HPLC
  3. additionwas added
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0aec2b7d11964268bdd963de1046b90f
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06969717B2

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