Sodium Hydroxide → HCID 71504395, compound

HRID 929342Notes

Reaction equation

HRID 929342 reaction equation
[CH2:1]([S:4]([N:7]([C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[C:16]([C:22]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][CH:28]=[N:27]3)=[O:23])[C:15]=1[F:34])S(CCC)(=O)=O)(=[O:6])=[O:5])[CH2:2][CH3:3].[OH-].[Na+]>CO>[F:34][C:15]1[C:16]([C:22]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][CH:28]=[N:27]3)=[O:23])=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=1[NH:7][S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86677170HCID 86677170, compound

Product 1

HCID 71504395HCID 71504395, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(propylsulfonyl)-N-(2,4,5-trifluoro-3-(quinoxaline-6-carbonyl)phenyl)propane-1-sulfonamide (60 mg, 0.12 mmol, 1 eq.) in MeOH (5 mL) was added NaOH (1N, 0.24 mL, 0.24 mmol, 2 eq.). The resulting mixture was stirred at rt for 1 h, then concentrated. The resulting residue was purified by flash column chromatography (PE/EA=1/1, v/v) to afford N-(2,4,5-trifluoro-3-(quinoxaline-6-carbonyl)phenyl)propane-1-sulfonamide (31.2 mg, 63.7%). LRMS (M−H+) m/z calculated 408.4, found 408.1. 1H NMR (CDCl3, 400 MHz) δ 8.95-8.99 (dd, 2 H), 8.45 (s, 1 H), 8.38-8.41 (dd, 1 H), 8.27-8.29 (d, 1 H), 7.70-7.77 (m, 1 H), 6.74 (s, 1 H), 3.13-3.17 (m, 2 H), 1.87-1.93 (m, 2 H), 1.06-1.10 (s, 3 H).

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified by flash column chromatography (PE/EA=1/1

Sources & evidence

ORD record
ord-3a20392f282f417dbcddcb12686e997e
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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