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

HRID 595393Notes

Reaction equation

HRID 595393 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cd38f7ba696b4bf1b43ebc8fc749d8dc
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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