Sodium Carbonate → HCID 67408796, compound

HRID 1401278Notes

Reaction equation

HRID 1401278 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:15]([C:16](=[O:18])[CH:17]=2)=[C:14]([O:19]C)[CH:13]=[C:12]([O:21]C)[C:11]=3[C@@H:23]2[CH2:27][CH2:26][N:25]([CH3:28])[C@H:24]2[CH2:29][OH:30])[CH:5]=[CH:6][CH:7]=1.Cl.N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[I:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:15]([C:16](=[O:18])[CH:17]=2)=[C:14]([OH:19])[CH:13]=[C:12]([OH:21])[C:11]=3[C@@H:23]2[CH2:27][CH2:26][N:25]([CH3:28])[C@H:24]2[CH2:29][OH:30])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 67409286HCID 67409286, compound

Product 1

HCID 67408796HCID 67408796, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of compound of example 68 (0.4 g, 0.70 mmol) and pyridine hydrochloride (0.327 g, 2.83 mmol) was heated at 180° C. for a period of 2.5 hours. The reaction mixture was diluted with methanol (60 mL) and basified with solid Na2CO3 to pH 10. The reaction mixture was filtered, and washed with methanol. The organic layer was concentrated and the residue purified by column chromatography using 0.01% ammonia and 4.5% methanol in chloroform as eluent to afford the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. concentrationThe organic layer was concentrated
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-3c5cfb62e3ab4284b2bb05a3d3b1e312
Source dataset
uspto-grants-2014_12
Patent number
US08906953B2

Reaction notes

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