Methanol → HCID 22046272, compound

HRID 1830723Notes

Reaction equation

HRID 1830723 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=2)=[O:12])=[C:6]([O:21][C:22]([F:25])([F:24])[F:23])[CH:5]=1.CO.O.[OH-].[Li+]>O>[CH3:20][C:17]1[N:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[CH:5][C:6]=2[O:21][C:22]([F:25])([F:23])[F:24])=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 67254164HCID 67254164, compound

Product 1

HCID 22046272HCID 22046272, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred suspension of 4-[3-(5-methyl-pyrazin-2-yl)-ureido]-3-trifluoromethoxy-benzoic acid methyl ester (136 mg, 0.37 mmol) in 4 mL 3:1 MeOH:H2O under nitrogen was added lithium hydroxide monohydrate (154 mg, 3.7 mmol), and the reaction heated to 65° C. The reaction turned yellow/green and eventually became a solution. After stirring overnight, the reaction was cooled to RT and partially concentrated by rotovap to remove most of the MeOH. The residual suspension was neutratized with 2N HCl until pH=6. The reaction formed a floculent precipitate which was filtered off with H2O and dried overnight under high vacuum to give the acid as a white solid (102 mg, 78%).

Workup

  1. temperaturethe reaction was cooled to RT
  2. concentrationpartially concentrated by rotovap
  3. customto remove most of the MeOH
  4. customThe reaction formed a floculent precipitate which
  5. filtrationwas filtered off with H2O
  6. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-50fc5324ab8e4ad1b6a586195047a9dc
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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