N-[2-cyclopropyl-7-(1,5-dimethyl-6-oxopyridin-3-yl)-1-benzofuran-5-yl]ethanesulfonamide → US10023592, Example 495

HRID 575844Notes

Reaction equation

HRID 575844 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>CO.[Pd]>[CH3:21][N:15]1[C:16](=[O:20])[C:17]([CH3:19])=[CH:18][C:13]([C:12]2[C:6]3[O:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:8][C:7]=3[CH:9]=[C:10]([NH:22][S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])[CH:11]=2)=[CH:14]1

Participants

4

Reactant 1

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

Product 1

HCID 118022156US10023592, Example 495Yield 14.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the title compound from Step 4 (70 mg, 0.18 mmol) and 10 mg of Pd/C in 40 mL of MeOH was stirred under a H2 atmosphere at room temperature for 1 h. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by prep-HPLC to give the title compound (10 mg, 14% yield) as a white solid. 1H NMR (CDCl3, 300 MHz): δ 7.77 (d, J=2.1 Hz, 1H), 7.56 (s, 1H), 7.04 (s, 1H), 7.01 (s, 1H), 6.26 (d, J=2.7 Hz, 1H), 4.88-4.84 (m, 1H), 3.61 (s, 3H), 3.34-3.26 (m, 1H), 3.09 (q, J=7.5 Hz, 2H), 2.90-2.84 (m, 1H), 2.21 (s, 3H), 1.87-1.82 (m, 1H), 1.72-1.63 (m, 1H), 1.56-1.43 (m, 2H), 1.38 (t, J=7.2 Hz, 3H), 0.98 (t, J=7.5 Hz, 3H). LCMS: 391 (M+1)+.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-e25489263f8c4d3f9663ee1f9708373b
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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