Pyridine → HCID 18957879, compound

HRID 2379079Notes

Reaction equation

HRID 2379079 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=C[CH:29]=[CH:28][CH:27]=1>>[CH3:27][CH:28]([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])[CH3:29]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 18957857HCID 18957857, compound

Product 1

HCID 18957879HCID 18957879, compound

Procedure

To a 25 ml round bottomed flask fitted with a magnetic stirrer bar, reflux condensor, and nitrogen inlet was added 1,6-dihydro-l-[2-(3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylicacid (0.20 g, 0.70 mmol) and thionyl chloride (5.0 ml). The mixture was heated at reflux for 2 hours, cooled to room temperature, and concentrated. The residue was suspended in 2-propanol (5.0 ml) and 4-dimethylaminopyridine (1 mg). Pyridine (0.17 ml, 2.1 mmol) was added with stirring at room temperature. After 16 hours, the reaction mixture was concentrated. Purification via flash column chromotography (silica gel, 5% methanol/dichloromethane) and repurification via medium pressure liquid chromotography (silica gel, 5% methanol/dichloromethane) gave the desired product, MP: 160°-161 ° C.

Workup

  1. customTo a 25 ml round bottomed flask fitted with a magnetic stirrer bar
  2. temperaturereflux condensor, and nitrogen inlet
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 2 hours
  5. concentrationconcentrated
  6. concentrationthe reaction mixture was concentrated
  7. customPurification
  8. customvia flash column chromotography (silica gel, 5% methanol/dichloromethane) and repurification via medium pressure liquid chromotography (silica gel, 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-daf05cf6a6804e40b1ea8913d0ac70d8
Source dataset
uspto-grants-1994_11
Patent number
US05360808

Reaction notes

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