Pyridine → HCID 59180461, compound

HRID 1925737Notes

Reaction equation

HRID 1925737 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[NH2:16][C:17]1[CH:21]=[CH:20][S:19][C:18]=1[C:22]([O:24][CH3:25])=[O:23].N1C=CC=CC=1>ClCCl>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([S:12]([NH:16][C:17]3[CH:21]=[CH:20][S:19][C:18]=3[C:22]([O:24][CH3:25])=[O:23])(=[O:14])=[O:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 27764754-(1H-pyrazol-1-yl)benzene-1-sulfonyl chloride

Product 1

HCID 59180461HCID 59180461, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1H-pyrazol-1-yl)benzene-1-sulfonyl chloride (0.5 g; 2.0 mmol) in dichloromethane (4.5 mL) at room temperature, was added methyl 3-aminothiophene-2-carboxylate (0.27 g; 1.7 mmol) followed by pyridine (0.27 g; 3.4 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 washed 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 crude residue was recrystallized from ethyl acetate/hexanes (1:9, v/v) to yield the title product as a tan/yellow solid (404 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washwashed 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 crude residue was recrystallized from ethyl acetate/hexanes (1:9, v/v)

Sources & evidence

ORD record
ord-2eeae8598da54c0e90ccf3bd85c2e152
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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