Trifluoroacetic acid → US10023592, Example 496

HRID 575845Notes

Reaction equation

HRID 575845 reaction equation
[CH:1]1([C:4]2[O:5][C:6]3[C:12]([C:13]4[CH:18]=[C:17]([CH3:19])[C:16](=[O:20])[N:15]([CH3:21])[CH:14]=4)=[CH:11][C:10]([NH:22][S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])=[CH:9][C:7]=3[CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>[SiH](CC)(CC)CC.C(Cl)Cl>[CH:1]1([CH:4]2[CH2:8][C:7]3[CH:9]=[C:10]([NH:22][S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])[CH:11]=[C:12]([C:13]4[CH:18]=[C:17]([CH3:19])[C:16](=[O:20])[N:15]([CH3:21])[CH:14]=4)[C:6]=3[O:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118021844N-[2-cyclopropyl-7-(1,5-dimethyl-6-oxopyridin-3-yl)-1-benzofuran-5-yl]ethanesulfonamide

Product 1

HCID 118021760US10023592, Example 496Yield 10%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 12052TriethylsilaneSolvent

Procedure

To a mixture of the title compound from Example 495, Step 4, (30 mg, 0.08 mmol) in Et3SiH (1 mL) in a sealed tube was added TFA (0.2 mL) at 0° C. It was allowed to warm up to room temperature and stirred overnight. The resulting mixture was diluted with DCM (30 mL) and washed with 1 N NaOH, water and brine. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was recrystallized from EtOAc to give the title compound (3 mg, 10% yield) as a white solid. 1H NMR (CDCl3, 300 MHz): δ 7.77 (s, 1H), 7.57 (s, 1H), 7.04 (d, J=3.0 Hz, 2H), 6.44 (s, 1H), 4.37-4.29 (m, 1H), 3.63 (s, 3H), 3.37-3.29 (m, 1H), 3.13-3.03 (m, 3H), 2.22 (s, 3H), 1.40 (t, J=7.5 Hz, 3H), 1.26-1.14 (m, 1H), 0.71-0.33 (m, 4H). LCMS: 389 (M+1)+.

Workup

  1. washwashed with 1 N NaOH, water and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-ce0f108a59544f20a43eb2ce977962e7
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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