Sodium Hydroxide → HCID 71268658, compound

HRID 929367Notes

Reaction equation

HRID 929367 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8](S(CCC)(=O)=O)[S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])=[CH:4][C:3]=1[C:21]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[N:26]2)=[O:22].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])=[CH:4][C:3]=1[C:21]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[N:26]2)=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71268570N-(4-fluoro-3-(quinoxaline-6-carbonyl)phenyl)-N-(propylsulfonyl)propane-1-sulfonamide

Product 1

HCID 71268658HCID 71268658, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-fluoro-3-(quinoxaline-6-carbonyl)phenyl)-N-(propylsulfonyl)propane-1-sulfonamide (50 mg, 0.10 mmol, 1.0 eq.) in MeOH (10 mL) was added NaOH aqueous solution (1 N, 0.22 mL, 0.22 mmol, 2.2 eq.). The resulting mixture was stirred at it for 1 h, then concentrated. The resulting residue was purified by flash column chromatography (PE/EA=1/1, v/v) to afford N-(4-fluoro-3-(quinoxaline-6-carbonyl)phenyl)propane-1-sulfonamide (33.4 mg, 89.5%). LRMS (M+H+) m/z calculated 374.1, found 374.1. 1H NMR (CDCl3, 400 MHz) δ 8.94-8.97 (dd, 2 H), 8.46-8.47 (m, 1 H), 8.31-8.34 (m, 1 H), 8.23-8.25 (m, 1 H), 7.50-7.54 (m, 1 H), 7.46-7.48 (m, 1 H), 7.19-7.23 (t, 1 H), 6.80 (s, 1 H), 3.10-3.14 (m, 2 H), 1.86-1.92 (m, 2 H), 1.04-1.08 (t, 3 H).

Workup

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

Sources & evidence

ORD record
ord-8da6cc9cb2d24947bd7c9d9688194e68
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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