Dichloromethane → 2,5-Di(4-pyridyl)-4-methylthiophen-3-ylmethylhydroxylamine trihydrochloride

HRID 2121731Notes

Reaction equation

HRID 2121731 reaction equation
C(OC([N:8]([CH2:17][C:18]1[C:22]([CH3:23])=[C:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[S:20][C:19]=1[C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)[O:9]C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+].C(Cl)[Cl:49]>>[ClH:49].[ClH:49].[ClH:49].[N:33]1[CH:34]=[CH:35][C:30]([C:19]2[S:20][C:21]([C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)=[C:22]([CH3:23])[C:18]=2[CH2:17][NH:8][OH:9])=[CH:31][CH:32]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 23434069HCID 23434069, compound

Product 1

HCID 234341062,5-Di(4-pyridyl)-4-methylthiophen-3-ylmethylhydroxylamine trihydrochloride

Procedure

To a stirred solution of N,O-di-tert-butoxycarbonyl-[2,5-di(4-pyridyl)-4-methylthiophen-3-yl]methylhydroxylamine (0.16 g) in CH2Cl2 (15 mL) was added trifluoroacetic acid (0.5 mL) and the mixture was stirred for 2 hours at room temperature. Trifluoroacetic acid (3 mL) was additionally added to the reaction mixture, and stirred for 2 hours. Saturated aqueous NaHCO3 solution was added to the reaction mixture and the whole was extracted with CH2Cl2 (100 mL×2). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-CH2Cl2 (1:1). The crude product was dissolved in 10% methanolic HCl (1 mL) and the volatiles were removed by evaporation. The resulting solid was recrystallized from diisopropyl ether to give the title compound (0.031 g).

Workup

  1. stirringstirred for 2 hours
  2. extractionthe whole was extracted with CH2Cl2 (100 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate-CH2Cl2 (1:1)
  8. dissolutionThe crude product was dissolved in 10% methanolic HCl (1 mL)
  9. customthe volatiles were removed by evaporation
  10. customThe resulting solid was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-7364670ed10146b2852b92c0595591a6
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

Loading…