Sodium Hydroxide → HCID 71268633, compound

HRID 1771124Notes

Reaction equation

HRID 1771124 reaction equation
[F:1][C:2]1[C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[N:13]3)=[O:9])=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[N:21](S(CCC)(=O)=O)[S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23].[OH-].[Na+]>CO>[F:1][C:2]1[C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[N:13]3)=[O:9])=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:23])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117902268HCID 117902268, compound

Product 1

HCID 71268633HCID 71268633, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2,4-difluoro-3-(quinoxaline-6-carbonyl)phenyl)-N-(propylsulfonyl)propane-1-sulfonamide (30 mg, 0.06 mmol, 1 eq.) in MeOH (5 mL) was added NaOH solution (1 N, 0.12 mL, 0.12 mmol, 2 eq.). The resulting mixture was stirred at rt for 1 h, then concentrated. The residue was purified via flash column (PE/EA=1/1, v/v) to afford N-(2,4-difluoro-3-(quinoxaline-6-carbonyl)phenyl)propane-1-sulfonamide (20 mg, 84.7%). LRMS (M−H+) m/z calculated 390.1. found 389.8. 1H NMR (CDCl3, 400 MHz) δ 8.93-8.98 (dd, 2H), 8.45 (s, 1H), 8.38-8.41 (m, 1H), 8.25-8.28 (m, 1H), 7.79-7.82 (m, 1H), 7.07-7.11 (t, 1H), 6.71 (s, 1H), 3.10-3.14 (m, 2H), 1.87-1.92 (m, 2H), 1.04-1.08 (t, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via flash column (PE/EA=1/1

Sources & evidence

ORD record
ord-76fc84ab01b14a7fb66687cd5728301b
Source dataset
uspto-grants-2016_02
Patent number
US09249110B2

Reaction notes

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