Trifluoroacetic acid → HCID 178448744, compound

HRID 1931136Notes

Reaction equation

HRID 1931136 reaction equation
[CH2:1]([N:5]1[N:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[S:7]/[C:6]/1=[N:14]\[C:15]([C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1[N:27](C(OC(C)(C)C)=O)/[N:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=1)=[O:16])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:5]1[N:9]=[C:8]([C:10]([CH3:11])([CH3:13])[CH3:12])[S:7]/[C:6]/1=[N:14]\[C:15](=[O:16])[C:17]1[CH:22]=[C:21]([C:23]([F:24])([F:26])[F:25])[CH:20]=[CH:19][C:18]=1[NH:27]/[N:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178448745HCID 178448745, compound

Product 1

HCID 178448744HCID 178448744, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 205B (120 mg, 0.19 mmol) in CH2Cl2 (5 mL) was treated with trifluoroacetic acid (0.15 mL, 1.9 mmol) at room temperature for 3 hours. The mixture was then concentrated under reduced pressure. The residue was treated with saturated aqueous NaHCO3 and extracted with EtOAc. The ethyl acetate layer was washed with water, brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and eluted with 1:1 hexanes-Et2O to afford 60 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.95 (t, J=7.5 Hz, 3H), 1.29-1.48 (m, 11H), 1.77-1.96 (m, 2H), 2.43-2.56 (m, 3H), 4.46 (t, J=7.3 Hz, 2H), 7.23 (d, J=6.8 Hz, 1H), 7.65-8.00 (m, 4H), 8.15 (s, 1H), 8.59 (d, J=1.7 Hz, 1H), 12.29 (s, 1H); MS (ESI+) m/z 519 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additionThe residue was treated with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. washThe ethyl acetate layer was washed with water, brine
  5. dry with materialdried with anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluted with 1:1 hexanes-Et2O

Sources & evidence

ORD record
ord-ba4fc8cb7f9343e4bdef699a7cd52815
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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