Lawesson's reagent → Methyl 5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-thiadiazole-2-carboxylate

HRID 595393

반응식

HRID 595393 반응식
[Cl:1][C:2]1[CH:17]=[C:16]([NH:18][CH:19]([CH3:21])[CH3:20])[C:5]([C:6]([NH:8][NH:9][C:10](=O)[C:11]([O:13][CH3:14])=[O:12])=O)=[CH:4][N:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[S:31][C:10]([C:11]([O:13][CH3:14])=[O:12])=[N:9][N:8]=2)=[C:16]([NH:18][CH:19]([CH3:21])[CH3:20])[CH:17]=1

참가 물질

5

반응물 2

HCID 87949Lawesson's reagentHCID 89689816Methyl 2-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-2-oxoacetate

생성물 1

HCID 89690804Methyl 5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-thiadiazole-2-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of methyl 2-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-2-oxoacetate (11) (1 g, 3.1 mmol) in THF (30 mL), Lawesson's reagent (6.3 mmol, 2 equiv) was added and heated to reflux for 3 h. The reaction mixture was diluted with EtOAc and washed twice with 10% NaHCO3 solution. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The crude material obtained was purified by column chromatography through silica gel and MeOH: DCM as eluent afford methyl 5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-thiadiazole-2-carboxylate.

후처리

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. washwashed twice with 10% NaHCO3 solution
  4. customThe organic layer was collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material obtained
  9. customwas purified by column chromatography through silica gel and MeOH

출처 및 근거

ORD 기록
ord-cd38f7ba696b4bf1b43ebc8fc749d8dc
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242975B2

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