Sodium Carbonate → HCID 67409414, compound

HRID 1401257Notes

Reaction equation

HRID 1401257 reaction equation
[Br:1][C:2]1[C:3]([Cl:31])=[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>[Br:1][C:2]1[C:3]([Cl:31])=[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 67397754HCID 67397754, compound

Product 1

HCID 67409414HCID 67409414, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of compound of example 28 (0.280 g, 0.550 mmol) and pyridine hydrochloride (0.780 g, 6.74 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-30abeabd2efd4c519eccf3481ba0294c
Source dataset
uspto-grants-2014_12
Patent number
US08906953B2

Reaction notes

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