HCID 136198174, compound → HCID 135873928, compound

HRID 454550Notes

Reaction equation

HRID 454550 reaction equation
[OH:1][C:2]1[CH:29]=[CH:28][C:27]([C:30]2[N:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][C:8]=1[C:9]([O:11]C(C)(C)C)=[O:10])=[O:5]>C(Cl)Cl.FC(F)(F)C(O)=O>[OH:1][C:2]1[CH:29]=[CH:28][C:27]([C:30]2[N:31]=[CH:32][CH:33]=[CH:34][N:35]=2)=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:19]=[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:17]=[CH:16][C:8]=1[C:9]([OH:11])=[O:10])=[O:5]

Participants

4

Reactant 1

HCID 136198174HCID 136198174, compound

Product 1

HCID 135873928HCID 135873928, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution mixture of the obtained tert-butyl 2-(2-hydroxy-5-(pyrimidin-2-yl)benzamido)-4-phenylbenzoate (5 mg) in methylene chloride (2 mL) and trifluoroacetic acid (0.50 mL) was stirred at room temperature for 3 hours and 30 minutes. The solvent was evaporated under reduced pressure, and water and chloroform were added to the residue. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 4 mg of 2-(2-hydroxy-5-(pyrimidin-2-yl)benzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and chloroform
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-72c00aab68f64424a1bf2145eda1c8e8
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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