Dimethyl Sulfoxide → HCID 69891786, compound

HRID 383094Notes

Reaction equation

HRID 383094 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:10][O:11][C:12](=[O:44])[C@H:13]([CH2:40][CH2:41][S:42][CH3:43])[NH:14][C:15](=[O:39])[C:16]1[CH:21]=[CH:20][C:19](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:18][C:17]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[CH3:45]S(C)=O>O.C(OCC)(=O)C>[CH3:10][O:11][C:12](=[O:44])[C@H:13]([CH2:40][CH2:41][S:42][CH3:43])[NH:14][C:15](=[O:39])[C:16]1[CH:21]=[CH:20][C:19](=[CH:45][O:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:18][C:17]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 20622838HCID 20622838, compound

Product 1

HCID 69891786HCID 69891786, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Hydroxypyridine (1.0 equivalent) is treated with sodium hydride (1.0 equivalent) in DMSO, then the resultant compound from Example 27A (1.0 equivalent) is added. When judged complete by TLC analysis, the reaction is diluted with water and ethyl acetate, the organic layer is dried and concentrated, and the crude title compound is purified by chromatography on silica gel.

Workup

  1. customthe organic layer is dried
  2. concentrationconcentrated
  3. customthe crude title compound is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7014365bcb604a248c5294dfe605c13e
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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