HCID 59408784, compound → HCID 25001115, compound

HRID 1188128Notes

Reaction equation

HRID 1188128 reaction equation
[CH3:1][N:2](C1CCCCO1)[C:3]1[S:4][C:5]([CH2:8][NH:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6][N:7]=1>C(O)(C(F)(F)F)=O.C(Cl)(Cl)Cl>[CH3:1][NH:2][C:3]1[S:4][C:5]([CH2:8][NH:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 59408784HCID 59408784, compound

Product 1

HCID 25001115HCID 25001115, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-methyl-N-(tetrahydro-2H-pyran-2-yl)-5-((thiazol-2-ylamino)methyl) thiazol-2-amine (50 mg, 0.16 mmol) in 10% TFA in CHCl3 (5 mL) was stirred at RT overnight. After evaporating the solvent, the residue was dissolved in MeOH, neutralized with Na2CO3 and extracted with CHCl3. The organic phase was dried, concentrated and purified by column chromatography yielding N-methyl-5-((thiazol-2-ylamino)methyl)thiazol-2-amine (28 mg, 77%) as a solid.

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in MeOH
  3. extractionextracted with CHCl3
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-a27ef617d8964f4891dd1b840f4bca0b
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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