Diisopropylethylamine → Piperidine-1-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 60622

Reaktionsgleichung

Reaktionsgleichung von HRID 60622
[N:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][NH2:18])=[N:15][CH:16]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][NH:18][C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])=[N:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2420851-Piperidinecarbonyl chlorideHCID 199167865-Fluoro-2-hydrazinylpyridine

Produkt 1

HCID 86686950Piperidine-1-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Piperidine carbonyl chloride (348 mg, 0.30 mL, 2.36 mmol) was added dropwise to a solution of 5-fluoro-2-hydrazinyl-pyridine (see for reference WO2010/022076, which is incorporated herein by reference; 0.30 g, 2.36 mmol) and DIPEA (1.20 mL, 7.08 mmol) in DCM (10 mL) at RT under nitrogen and the mixture stirred for 2 h. The solution was washed with water (2×15 mL) and dried (Na2SO4). The solvent was evaporated and the residue triturated (diethyl ether) to afford Intermediate Da (475 mg, 84%). LCMS (Method 1): Rt 1.82 min, m/z 239 [MH+].

Aufarbeitung

  1. washThe solution was washed with water (2×15 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated
  4. customthe residue triturated (diethyl ether)
  5. customto afford Intermediate Da (475 mg, 84%)

Quellen und Nachweise

ORD-Eintrag
ord-60030f13404346cd934de8be016da2f6
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440974B2

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