Sodium Hydroxide → HCID 71504585, compound

HRID 929357Notes

Reaction equation

HRID 929357 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([C:20]2[C:21]([F:41])=[C:22]([N:28](S(CCC)(=O)=O)[S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])[CH:23]=[C:24]([F:27])[C:25]=2[F:26])=[O:19])=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([C:20]2[C:21]([F:41])=[C:22]([NH:28][S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])[CH:23]=[C:24]([F:27])[C:25]=2[F:26])=[O:19])=[CH:13][CH:12]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86677181HCID 86677181, compound

Product 1

HCID 71504585HCID 71504585, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a N-(3-(3-(4-chlorophenyl)quinoxaline-6-carbonyl)-2,4,5-trifluorophenyl)-N-(propylsulfonyl)propane-1-sulfonamide (50 mg, 0.08 mmol, 1.0 eq.) in MeOH (5 mL) was added NaOH aqueous solution (1 N, 0.16 mL, 0.16 mmol, 2.0 eq.). The resulting mixture was stirred at rt for 1 h, then concentrated. The resulting residue was purified by flash column chromatography (PE/EA=2/1, v/v) to afford N-(3-(3-(4-chlorophenyl)quinoxaline-6-carbonyl)-2,4,5-trifluorophenyl)propane-1-sulfonamide (25 mg, 60.2%). LRMS (M−H+) m/z calculated 518.1, found 518.0. 1H NMR (CDCl3, 400 MHz) δ 9.42 s), 8.44 (s, 1 H), 8.27-8.38 (m, 2 H), 8.14-8.16 (dd, 2 H), 7.73-7.76 (m, 1 H), 7.55-7.57 (dd, 2 H), 6.55 (s, 1 H), 3.14-3.18 (m, 2 H), 1.88-1.94 (q, 2 H), 1.06-1.10 (t, 3 H).

Workup

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

Sources & evidence

ORD record
ord-94d4fe5056514abbbea3056ebd86abba
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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