Sodium Carbonate → HCID 67408710, compound

HRID 1401268Notes

Reaction equation

HRID 1401268 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:20]([C:21](=[O:23])[CH:22]=1)=[C:19]([O:24]C)[CH:18]=[C:17]([O:26]C)[C:16]=2[C@@H:28]1[CH2:32][CH2:31][N:30]([CH3:33])[C@H:29]1[CH2:34][OH:35].Cl.N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:20]([C:21](=[O:23])[CH:22]=1)=[C:19]([OH:24])[CH:18]=[C:17]([OH:26])[C:16]=2[C@@H:28]1[CH2:32][CH2:31][N:30]([CH3:33])[C@H:29]1[CH2:34][OH:35]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 89261805HCID 89261805, compound

Product 1

HCID 67408710HCID 67408710, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of compound of example 48 (0.650 g, 1.30 mmol) and pyridine hydrochloride (1.5 g, 12.90 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 yield the title compound as a yellow solid.

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-c32f85a48f114c8bb7f41ac0a03677bb
Source dataset
uspto-grants-2014_12
Patent number
US08906953B2

Reaction notes

Loading…