Benzylamine → Ethyl 3-methyl-7-benzylaminothieno[3,2-b]pyridine-6-carboxylate

HRID 2107617Notes

Reaction equation

HRID 2107617 reaction equation
[CH3:1][C:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10](Cl)=[C:5]2[S:4][CH:3]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([NH:24][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:5]2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 23046143Ethyl 3-methyl-7-chlorothieno[3,2-b)pyridine-6-carboxylate

Product 1

HCID 23046158Ethyl 3-methyl-7-benzylaminothieno[3,2-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 3-methyl-7-chlorothieno[3,2-b)pyridine-6-carboxylate (3.0 g, 0.0117 mol) and benzylamine (2.5 g, 0.0234 mol) were heated in an oil-bath with stirring for 30 minutes (oil-bath temperature to 220°). On cooling the residue was dissolved in chloroform, washed with dilute aqueous sodium hydroxide and the aqueous phase back-extracted with more chloroform. The combined chloroform extracts were washed with water, dried and evaporated to give an oil. This oil was purified by flash chromatography on silica (40-60 mesh) with dichloromethane as eluant to give an oil which crystallised on standing. Recrystallisation from methanol gives the title compound as pale yellow crystals, 3.0 g, m.p. 99°-100°.

Workup

  1. temperatureOn cooling the residue
  2. washwashed with dilute aqueous sodium hydroxide
  3. extractionthe aqueous phase back-extracted with more chloroform
  4. washThe combined chloroform extracts were washed with water
  5. customdried
  6. customevaporated
  7. customto give an oil
  8. customThis oil was purified by flash chromatography on silica (40-60 mesh) with dichloromethane as eluant
  9. customto give an oil which
  10. customcrystallised
  11. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-613ade682fc14acea109e2237a55adf9
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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