Picolinic acid → Mls000737262

HRID 1908854노트

반응식

HRID 1908854 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

HCID 267294Mls000737262수율 3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5a561a1f020e46f3bf5b72a2dd4883a9
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598208B2

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