Water → 4-Aza-spiro[2,5]octane-4-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 1402412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402412
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH2:10]1[C:12]2([CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[C:18](Cl)=[O:19])[CH2:11]1.CCN(C(C)C)C(C)C.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:18]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]32[CH2:10][CH2:11]3)=[O:19])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 866872634-Aza-spiro[2.5]octane-4-carbonyl chloride

Produkt 1

HCID 866872644-Aza-spiro[2,5]octane-4-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A red solution of (5-fluoro-pyridin-2-yl)-hydrazine (477 mg, 3.75 mmol), Intermediate 148a (3.00 mmol) and DIPEA (0.78 mL, 4.5 mmol) in DCM (20 mL) was stirred at reflux for 40 h. To the cooled solution was added water (20 mL) and the mixture shaken. The aqueous was extracted with DCM (2×10 mL), then the combined organics passed through a hydrophobic frit and concentrated in vacuo. Flash chromatography (silica 40 g, 1-5% [2M NH3 in MeOH] in DCM) gave the title compound as a yellow solid (587 mg, 74%). LCMS (Method 3): Rt 2.66 min, m/z 265 [MH+].

Aufarbeitung

  1. temperatureat reflux for 40 h
  2. extractionThe aqueous was extracted with DCM (2×10 mL)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1dfb03d8fb974533836e864379d66746
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907094B2

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