2,2,2-Trifluoroethylhydrazine → 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-N'-(2,2,2-trifluoroethyl)-3-pyridinecarboxylic acid hydrazide

HRID 240682

Reaktionsgleichung

Reaktionsgleichung von HRID 240682
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([OH:22])=O)[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.[F:23][C:24]([F:29])([F:28])[CH2:25][NH:26][NH2:27].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([NH:27][NH:26][CH2:25][C:24]([F:29])([F:28])[F:23])=[O:22])[CH:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:18])([F:17])[F:19])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 787402,2,2-TrifluoroethylhydrazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666869715-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid

Produkt 1

HCID 715095645-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-N'-(2,2,2-trifluoroethyl)-3-pyridinecarboxylic acid hydrazideAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-(4-Chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (1000 mg, 3.02 mmol; CAN 1018782-82-5) and (2,2,2-trifluoroethyl)hydrazine (380 mg, 3.33 mmol; CAN 5042-30-8) were combined with DMF (10 mL) to give a colorless solution. TBTU (1.06 g, 3.32 mmol) and DIPEA (1.56 g, 2.05 mL, 12.1 mmol) were added. The reaction mixture was stirred for 15 h at room temperature. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layers were combined and washed with water (1×50 mL) and brine (1×50 mL). The organic layers were dried with MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 50 g, 0% to 50% EtOAc in hexane) to give the title compound (0.35 g, 27%) as white solid; LC-MS (UV peak area/ESI) 100%, 426.0451 (M−H)−.

Aufarbeitung

  1. customto give a colorless solution
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washwashed with water (1×50 mL) and brine (1×50 mL)
  4. dry with materialThe organic layers were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica gel, 50 g, 0% to 50% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-65f54d75a99b4aeba4cc86a4d0fb2e44
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648099B2

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