Methanol → Methyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)picolinate

HRID 1184944Notes

Reaction equation

HRID 1184944 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[NH:10][C:11]2[CH:26]=[CH:25][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([OH:24])=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].S(=O)(=O)(O)O.[CH3:37]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:27])[NH:10][C:11]2[CH:26]=[CH:25][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24][CH3:37])=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:28]([F:31])([F:29])[F:30]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 59772925Sorafenib related compound 10

Product 1

HCID 10217230Methyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)picolinateYield 90%

Procedure

4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)picolinic acid (0.5 g, 1.11 mmol) was suspended in methanol (10 mL). Concentrated sulfuric acid (2 mL) was added at room temperature, and the resulted mixture was refluxed for 3 hours. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (dichloromethane:methanol=10:1) to give methyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)picolinate A11 (0.46 g, purity 95%, yield 90%) as a white solid.

Workup

  1. temperaturethe resulted mixture was refluxed for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-9d3a2644d9ef47ccb3de56413159e861
Source dataset
uspto-grants-2014_03
Patent number
US08669369B2

Reaction notes

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