Picolinic acid → Mls000737262

HRID 1908854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908854
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](O)=O.CCN(C(C)C)C(C)C.CN(C(O[N:27]1[N:35]=[N:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1C=CC=CC=1C(NN)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:60])=CC=1>C(Cl)Cl.CC(=O)OCC>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:60][C:28]([C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][N:34]=2)=[N:27][N:35]=1

Komponenten

8

Edukt 5

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 87949Lawesson's reagentHCID 255881PicolinohydrazideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 267294Mls000737262Ausbeute 3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the appropriate pyridine-carboxylic acid (1 eq.) and DIPEA (3 eq.) in DCM (20 mL/mmol), TBTU (1 eq.) is added. The mixture is stirred for 5 min before the appropriate pyridine-carboxylic acid hydrazide (1 eq.) is added. The mixture is stirred at rt for 1 h before it is diluted with DCM, washed with water, dried over MgSO4, filtered and concentrated. The remaining residue is dissolved in THF, Lawesson's reagent (2 eq.) is added and the mixture is stirred at 110° C. for 6 min under microwave irradiation. The mixture is diluted with EA, washed with sat. aq. NaHCO3, and concentrated. The crude product is purified by chromatography on prep. TLC plates or by prep. HPLC to give the desired 2,5-dipyridyl-[1,3,4]thiadiazole in 3-44% yield.

Aufarbeitung

  1. additionis added
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe remaining residue is dissolved in THF
  7. stirringthe mixture is stirred at 110° C. for 6 min under microwave irradiation
  8. washwashed with sat. aq. NaHCO3
  9. concentrationconcentrated
  10. customThe crude product is purified by chromatography on prep

Quellen und Nachweise

ORD-Eintrag
ord-5a561a1f020e46f3bf5b72a2dd4883a9
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598208B2

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