Pyridine → HCID 59180417, compound

HRID 1925741Notes

Reaction equation

HRID 1925741 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:13](Cl)(=[O:15])=[O:14])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[NH2:17][C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:23]([O:25][CH3:26])=[O:24].N1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([S:13]([NH:17][C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])(=[O:15])=[O:14])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 59180422HCID 59180422, compound

Product 1

HCID 59180417HCID 59180417, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 121(1.5 g; 5.5 mmol) in dichloromethane (14 mL) at room temperature, methyl 3-aminothiophene-2-carboxylate (0.86 g; 5.5 mmol) was added followed by pyridine (0.87 g; 11.0 mmol) and then stirred at room temperature under a nitrogen atmosphere for 24 hours. The reaction mixture was concentrated under reduced pressure and then taken up in ethyl acetate (20 mL) and extracted with water. The aqueous layer was separated and extracted with ethyl acetate (2×20 mL). The combined organic phases were successively washed with water and aqueous saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 40% v/v over 900 mL gradient elution) to give the title product as a light red solid (86 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with water
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washThe combined organic phases were successively washed with water and aqueous saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude residue was purified by automated silica gel column chromatography (Biotage®)
  10. washeluting with ethyl acetate/hexanes (0 to 40% v/v over 900 mL gradient elution)

Sources & evidence

ORD record
ord-d5523cb73f1043578d8b74ecb6d26edf
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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