Water → HCID 10431879, compound

HRID 2355001Notes

Reaction equation

HRID 2355001 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[N:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[OH:18][C:19]1[CH:20]=[C:21]([O:33][CH:34]([CH3:36])[CH3:35])[CH:22]=[C:23]([CH:32]=1)[C:24]([NH:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1)=[O:25].O>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:18][C:19]2[CH:32]=[C:23]([C:24](=[O:25])[NH:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH:22]=[C:21]([O:33][CH:34]([CH3:36])[CH3:35])[CH:20]=2)=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 230930393-Hydroxy-5-[(propan-2-yl)oxy]-N-(1,3-thiazol-2-yl)benzamide

Product 1

HCID 10431879HCID 10431879, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

After adding 123 mg (0.72 mmol) of 6-chloronicotinic acid methyl ester and 199 mg (1.44 mmol) of potassium carbonate to a solution of 100 mg (0.36 mmol) of the obtained amide compound in N,N-dimethylfommamide (10.0 ml), the mixture was stirred at 80° C. for 18 hours under a nitrogen atmosphere. Water was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layer was dried and then concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to obtain the title compound as a white solid. The analysis data for the compound obtained in Production Example 65 are shown below.

Workup

  1. customthe organic layer was dried
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f9583c8db9a1475abb7430f6e7f34243
Source dataset
uspto-grants-2010_07
Patent number
US07754743B2

Reaction notes

Loading…