Trifluoroacetic acid → HCID 118062734, compound

HRID 920840Notes

Reaction equation

HRID 920840 reaction equation
[C:1]([C:4]1[C:5]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=2)=[N:6][N:7]2[CH2:12][C:11]3([CH2:14][CH2:13]3)[N:10](C(OC(C)(C)C)=O)[CH2:9][C:8]=12)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:29][C:24]1[CH:23]=[C:22]([C:5]2[C:4]([C:1]([NH2:2])=[O:3])=[C:8]3[CH2:9][NH:10][C:11]4([CH2:14][CH2:13]4)[CH2:12][N:7]3[N:6]=2)[CH:27]=[CH:26][C:25]=1[F:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118071191HCID 118071191, compound

Product 1

HCID 118062734HCID 118062734, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 350G (0.29 g, 0.689 mmol) in DCM (5 mL) was added TFA (3 mL) and the resulting solution was stirred at RT for 2 h. The volatiles were removed under reduced pressure. The residue was basified with a 10% aqueous solution of NaHCO3 and extracted with EtOAc (3×20 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated to afford Intermediate 350H as a yellow solid (0.2 g, 85%). MS(ES): m/z=321 [M+H]+; 1H NMR (300 MHz, chloroform-d) δ ppm 7.71 (dd, J=7.2, 2.3 Hz, 1H), 7.51 (ddd, J=8.3, 4.5, 2.3 Hz, 1H), 7.33-7.11 (m, 1H), 5.33 (br. s., 2H), 4.40 (s, 2H), 4.03 (s, 2H), 1.02-0.88 (m, 2H), 0.80-0.59 (m, 2H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-3e3fe69b0aed4218adc4bcbbaa924a12
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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