Trifluoroacetic acid → HCID 86271301, compound

HRID 528003Notes

Reaction equation

HRID 528003 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C:11]1[C:12]2[CH:19]=[C:18]([C:20]3[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH:25]=3)[NH:17][C:13]=2[N:14]=[CH:15][N:16]=1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C:11]1[C:12]2[CH:19]=[C:18]([C:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=3)[NH:17][C:13]=2[N:14]=[CH:15][N:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86271300HCID 86271300, compound

Product 1

HCID 86271301HCID 86271301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 66B (220 mg, 0.502 mmol) in 5 mL dichloromethane was added 2,2,2-trifluoroacetic acid (0.387 ml, 5.02 mmol). The reaction was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was dried under high-vacuum for 2 hours. The residue was dissolved with 3 mL methanol, and the mixture was treated with excess 2 M hydrochloric acid/diethyl ether followed by stirring for 20 minutes. The mixture was then diluted with 50 mL diethyl ether, and the solid was collected by filtration. The collected solid was dried under high-vacuum to give the title compound as a hydrochloride salt. 1H NMR (400 MHz, DMSO-d6) δ 13.48 (s, 1H) 9.64 (s, 2H) 9.08 (s, 1H) 7.42-7.59 (m, 2H) 7.32 (dd, J=9.16, 4.27 Hz, 1H) 6.80 (d, J=35.71 Hz, 2H) 4.15 (q, J=6.92 Hz, 3H) 3.84 (s, 2H) 3.31 (s, 2H) 2.77 (s, 1H) 1.07-1.28 (m, 3H). MS (ESI+) m/z 339.1 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was dried under high-vacuum for 2 hours
  3. dissolutionThe residue was dissolved with 3 mL methanol
  4. additionthe mixture was treated with excess 2 M hydrochloric acid/diethyl ether
  5. stirringby stirring for 20 minutes
  6. additionThe mixture was then diluted with 50 mL diethyl ether
  7. filtrationthe solid was collected by filtration
  8. customThe collected solid was dried under high-vacuum

Sources & evidence

ORD record
ord-4cd4483ae97744f89ab3f2c5e5a9144a
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

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