Pyridine → HCID 8823202, compound

HRID 1925743Notes

Reaction equation

HRID 1925743 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10](Cl)(=[O:12])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH2:14][C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]([O:22][CH3:23])=[O:21].N1C=CC=CC=1>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10]([NH:14][C:15]3[CH:19]=[CH:18][S:17][C:16]=3[C:20]([O:22][CH3:23])=[O:21])(=[O:12])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 3142583Indan-5-sulfonyl chloride

Product 1

HCID 8823202HCID 8823202, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dihydro-1H-indene-5-sulfonyl chloride (0.5 g; 2.3 mmol) in dichloromethane (5 mL) at room temperature, methyl 3-aminothiophene-2-carboxylate (0.3 g; 1.9 mmol) was added followed by pyridine (0.32 g; 4.0 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 (50 mL) and extracted with water. The aqueous layer separated and extracted with ethyl acetate (2×50 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 recrystallized from acetonitrile to yield the title product as a white solid (0.3 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with water
  3. customThe aqueous layer separated
  4. extractionextracted with ethyl acetate (2×50 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 recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2de22024a0c14691b97c47461c236f94
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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