Pyridine → HCID 59180392, compound

HRID 1925714Notes

Reaction equation

HRID 1925714 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([Cl:15])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[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>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:16][C:17]2[CH:21]=[CH:20][S:19][C:18]=2[C:22]([O:24][CH3:25])=[O:23])(=[O:13])=[O:12])=[C:7]([Cl:15])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 59180415HCID 59180415, compound

Product 1

HCID 59180392HCID 59180392, compoundYield 49.3%

Procedure

A solution of 70 (2.5 g; 9.36 mmol) and methyl 3-aminothiophene-2-carboxylate (1.62 g; 10.30 mmol) in anhydrous pyridine (12.0 mL; 144 mmol) was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 20% v/v) to give the title compound as a clear oil (1.79 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by automated silica gel column chromatography (Biotage®)
  3. washeluting with ethyl acetate/hexanes (0 to 20% v/v)

Sources & evidence

ORD record
ord-ef1663f8111a47fcaefb5241a4cb4cc2
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

Loading…