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

HRID 630952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 630952
[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-fb93be6094144490bfe7090a15547f57
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315503B2

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