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Triethylamine → 3-Bromo-5-[1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)cyclopropyl]pyridine

HRID 1521609
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1521609
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.O[N:15]=[C:16]([CH:18]1[CH2:20][CH2:19]1)[NH2:17].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2([C:11]3[O:13][N:17]=[C:16]([CH:18]4[CH2:20][CH2:19]4)[N:15]=3)[CH2:9][CH2:10]2)[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 595784161-(5-Bromopyridin-3-YL)cyclopropane-1-carboxylic acid

Produkt 1

HCID 899617073-Bromo-5-[1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)cyclopropyl]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the title compound from Example 72 Step A (45 mg, 0.19 mmol), N′-hydroxycyclopropanecarboximidamide (22 mg, 0.22 mmol) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (116 mg, 0.223 mmol) in N,N-dimethylformamide (0.93 mL) was added triethylamine (26 μl, 0.19 mmol). The reaction stirred at room temperature overnight. It was then diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was then diluted with toluene and heated to reflux overnight. Purification by flash chromatography on silica gel (10-100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 307.85 [M+2+H]+.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionThe resulting material was then diluted with toluene
  7. temperatureheated
  8. temperatureto reflux overnight
  9. customPurification by flash chromatography on silica gel (10-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7499308e2ffc41a4bd1c927c130a6870
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09073929B2

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