Pyridine → HCID 67828555, compound

HRID 2379078Notes

Reaction equation

HRID 2379078 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]([OH:21])=[O:20])=[CH:13]2)=[O:8])[CH:2]=1.S(Cl)(Cl)=O.N1C=CC=[CH:28][CH:27]=1>>[CH2:27]([O:20][C:19]([C:14]1[CH:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][CH2:10][NH:9][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:8])[CH:13]=1)=[O:21])[CH3:28]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 18957857HCID 18957857, compound

Product 1

HCID 67828555HCID 67828555, compound

Procedure

To a 10 ml round bottomed flask fitted with a magnetic stirrer bar, reflux condensor, and nitrogen inlet was added 1,6-dihydro-1-[2-(3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylicacid (0.14 g, 0.49 mmol) and thionyl chloride (3.0 ml). The mixture was heated for 1 hour at reflux, cooled to room temperature, and concentrated. The residue was suspended in absolute ethanol (7.0 ml) and 4-dimethylaminopyridine (1 mg). Pyridine (0.12 ml, 1.47 mmol) was added with stirring at room temperature. After 16 hours, the mixture was concentrated. Purification via medium liquid chromotography (silica gel, 5-10% methanol/dichloromethane) gave the desired ester, MP: 240°-242° C.

Workup

  1. customTo a 10 ml round bottomed flask fitted with a magnetic stirrer bar
  2. temperaturereflux condensor, and nitrogen inlet
  3. temperatureThe mixture was heated for 1 hour
  4. temperatureat reflux
  5. concentrationconcentrated
  6. concentrationthe mixture was concentrated
  7. customPurification via medium liquid chromotography (silica gel, 5-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-09034f6e69184013b0b01aa8ecd4455a
Source dataset
uspto-grants-1994_11
Patent number
US05360808

Reaction notes

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