Sodium Hydroxide → HCID 11359669, compound

HRID 1432331Notes

Reaction equation

HRID 1432331 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[C:12]([C:28]#[C:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[CH3:27][N:25]([CH3:26])[C:22]1[CH:21]=[CH:20][C:19]([C:17]2[CH:18]=[C:13]3[C:12]([C:28]#[C:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:11][NH:10][C:14]3=[N:15][CH:16]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86613122HCID 86613122, compound

Product 1

HCID 11359669HCID 11359669, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To sulfonamide 21 (36.9 mg, 0.077 mmol) in EtOH (770 μL) was added 10% aq. NaOH (386 μL) and the reaction mixture heated at 90° C. for 1 h. It was then poured onto water (5 mL), extracted with ethyl acetate (4×10 mL) and the combined organic extracts dried (MgSO4) and concentrated. The residue was purified by preparative LCMS (column LUNA 10μ C18(2) 00G4253-V0 250×50 mm) using water-acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give inhibitor 22 as a white solid (7.3 mg, 28%); 1H NMR (400 MHz, CDCl3) δ 6.86 (d, J=8.85 Hz, 2H), 7.31-7.39 (m, 3H), 7.57-7.62 (m, 5H), 8.24 (d, J=1.87 Hz, 1H), 8.59 (d, J=1.80 Hz, 1H), 9.83 (bs, 1H).

Workup

  1. additionIt was then poured onto water (5 mL)
  2. extractionextracted with ethyl acetate (4×10 mL)
  3. dry with materialthe combined organic extracts dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by preparative LCMS (column LUNA 10μ C18(2) 00G4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-0b9edc90c7d1444788a112a092d336bc
Source dataset
uspto-grants-2009_11
Patent number
US07612086B2

Reaction notes

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