Trifluoroacetic acid → HCID 59170903, compound

HRID 1362639Notes

Reaction equation

HRID 1362639 reaction equation
C([O:5][C:6](=O)/[C:7](=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]2)=[C:22]([O:32][CH3:33])[CH:21]=1)/[CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][N:10]1[CH2:9][CH2:8]/[C:7](=[CH:19]\[C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]3)=[C:22]([O:32][CH3:33])[CH:21]=2)/[C:6]1=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66960724HCID 66960724, compound

Product 1

HCID 59170903HCID 59170903, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (0.5 mL) solution of (E)-4-(3-fluorobenzylamino)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]butyric acid tert-butyl ester (4.50 mg), trifluoroacetic acid (500 μL) was added. After agitating reaction solution at room temperature for 1.5 hours and agitating that materials disappeared, reaction solution was concentrated under reduced pressure as it was. The residue was dissolved in DMF (0.5 mL), IPEA (17.0 μL), EDC (5.58 mg), and HOBT (3.93 mg) were added to the reaction solution one by one, and the reaction solution was agitated at room temperature for 1.5 hours. After confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate:ethanol=20:1), and 2.30 mg of the title compound was obtained.

Workup

  1. customreaction solution at room temperature for 1.5 hours
  2. stirringagitating that materials
  3. customreaction solution
  4. concentrationwas concentrated under reduced pressure as it
  5. dissolutionThe residue was dissolved in DMF (0.5 mL)
  6. additionIPEA (17.0 μL), EDC (5.58 mg), and HOBT (3.93 mg) were added to the reaction solution one by one
  7. stirringthe reaction solution was agitated at room temperature for 1.5 hours
  8. additionwere added to the reaction solution
  9. customthe organic layer was partitioned
  10. washAfter the obtained organic layer was washed with a saturated saline solution, it
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate:ethanol=20:1)

Sources & evidence

ORD record
ord-00d7a465d84b4413be924d67cc4dc9bd
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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