Methyl iodide → 2-chloro-N-isopropyl-5-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyridin-4-amine

HRID 595424Notes

Reaction equation

HRID 595424 reaction equation
[CH3:1]I.[Cl:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([SH:15])=[N:12][N:11]=2)=[C:6]([NH:16][CH:17]([CH3:19])[CH3:18])[CH:5]=1>CO>[Cl:3][C:4]1[CH:5]=[C:6]([NH:16][CH:17]([CH3:19])[CH3:18])[C:7]([C:10]2[O:14][C:13]([S:15][CH3:1])=[N:12][N:11]=2)=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178456766HCID 178456766, compound

Product 1

HCID 896909252-chloro-N-isopropyl-5-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl iodide (22 mmol, 2 equiv.) was added to a solution of 5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazole-2-thiol (42) (1.5 g, 5.5 mmol) in MeOH (10 mL). The reaction mixture was stirred overnight at room temperature. The reaction mass was concentrated under reduced pressure. The crude material obtained was purified by column chromatography through silica gel and MeOH: DCM as eluent to furnish the desired compound, 2-chloro-N-isopropyl-5-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyridin-4-amine (43). LC/MS: Purospher@star RP-18, 4×55 mm, 3 μm; Solvent A=10% ACN: 90% H2O: 20 mM NH4OAc; Solvent B=90% ACN: 10% H2O: 20 mM NH4COOAc; gradient 0-100% B over 1.5 min (3.2 min run time); retention time: 1.994 min; LCMS (ES-API), m/z 285.1 (M+H).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customThe crude material obtained
  3. customwas purified by column chromatography through silica gel and MeOH

Sources & evidence

ORD record
ord-555c0e40320a4e9f8da44419e8288ca3
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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