Trifluoroacetic acid → HCID 66893959, compound

HRID 736472Notes

Reaction equation

HRID 736472 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:32])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]2[N:29]=[C:28]([NH2:30])[N:27]=[C:26]([NH2:31])[N:25]=2)=[CH:18][CH:17]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:32])[C:16]1[CH:17]=[CH:18][C:19]([CH:22]=[CH:23][C:24]2[N:25]=[C:26]([NH2:31])[N:27]=[C:28]([NH2:30])[N:29]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66891660HCID 66891660, compound

Product 1

HCID 66893959HCID 66893959, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution at room temperature of 219 (25 mg, 0.056 mmol) in CH2Cl2 (1.5 mL) was added TFA (0.3 mL, 4.3 mmol). After 30 min, a solution of sat. NaHCO3 was slowly added until pH 8 is reached, CH2Cl2 was removed under reduced pressure, AcOEt was added, and the phases were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography on silica gel (MeOH/CH2Cl2: 10/90) to afford the title compound 220 (19 mg, 0.054 mmol, 98% yield). 1H NMR (300 MHz, acetone-d6) δ (ppm): 8.33, 8.13 (2d, J=7.5 Hz, 1H), 8.22 (d, J=15.9 Hz, 1H), 8.01 (d, J=8.1 Hz, 2H), 7.84 (d, J=8.1 Hz, 2H), 7.38-6.96 (m, 2H), 7.03 (d, J=15.9 Hz, 1H), 6.94-6.62 (m, 2H).

Workup

  1. customCH2Cl2 was removed under reduced pressure, AcOEt
  2. additionwas added
  3. customthe phases were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash chromatography on silica gel (MeOH/CH2Cl2: 10/90)

Sources & evidence

ORD record
ord-763e522a04a04391b17ab79f5c2ced47
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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