Picolinic acid → MLS000737262

HRID 1908854Notes

Reaction equation

HRID 1908854 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

HCID 267294MLS000737262Yield 3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5a561a1f020e46f3bf5b72a2dd4883a9
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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