Trifluoroacetic acid → HCID 71293414, compound

HRID 570894Notes

Reaction equation

HRID 570894 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:34])[N:20]([CH2:22][CH2:23][CH2:24][N:25]([C:27](OC(C)(C)C)=[O:28])[CH3:26])[N:21]=[C:8]2[N:7]([C:35]2[CH:40]=CC=[C:37]([C:41](F)(F)F)[CH:36]=2)[C:6]=1[CH3:45])=[O:4].[C:46](O)([C:48]([F:51])([F:50])[F:49])=O.[CH2:53](N(CC)CC)C.C(OC(=O)C)(=O)C>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:34])[N:20]([CH2:22][CH2:23][CH2:24][N:25]([C:27](=[O:28])[CH3:53])[CH3:26])[N:21]=[C:8]2[N:7]([C:35]2[CH:36]=[CH:37][CH:41]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:40]=2)[C:6]=1[CH3:45])=[O:4]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 71293456HCID 71293456, compound

Product 1

HCID 71293414HCID 71293414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 18 (0.12 g, 0.19 mmol) in DCM (2.5 mL), was added TFA (0.25 mL). The resulting mixture was stirred at RT for 1 hour, and then evaporated in vacuo. The resulting residue was taken up in DCM (4 mL), and triethylamine (86 μL, 0.62 mmol) was added, followed by acetic anhydride (47 μL, 0.50 mmol). The reaction mixture was stirred at RT for 30 mins and was then partitioned between EtOAc and water. The organic layer was separated, and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient 0-10% MeOH in DCM to yield the title compound as a white solid (80 mg).

Workup

  1. customevaporated in vacuo
  2. stirringThe reaction mixture was stirred at RT for 30 mins
  3. customwas then partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer further extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with a gradient 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-fce4275d382a4845bfade1a875ee5d5c
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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