Sodium Hydroxide → HCID 178420919, compound

HRID 2114060Notes

Reaction equation

HRID 2114060 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[NH:23][CH:22]=[N:21][N:20]=4)[CH:18]=[C:13]3[C:12]([C:24]3[CH:28]=[CH:27][O:26][CH:25]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[O:26]1[CH:27]=[CH:28][C:24]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([C:19]4[NH:23][CH:22]=[N:21][N:20]=4)[CH:18]=3)[NH:10][CH:11]=2)=[CH:25]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178527313HCID 178527313, compound

Product 1

HCID 178420919HCID 178420919, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 40 (60 mg, 0.15 mmol), EtOH (1.54 mL) and 10% aq. NaOH (767 μL) were heated at 90° C. for 45 min then cooled and poured onto water (11 mL) and extracted with ethyl acetate (4×10 mL). The combined organic extracts were dried (MgSO4), concentrated and the residue purified by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give the product as a white solid (10.7 mg, 28%); 1H NMR (400 MHz, CDCl3+2 drops CD3OD) δ 6.70 (d, J=1.0 Hz, 1H), 7.45 (s, 1H), 7.49 (t, J=1.5 Hz, 1H), 7.89 (s, 1H), 8.16 (bs, 1H), 8.75 (d, J=1.9 Hz, 1H), 8.92 (s, 1H).

Workup

  1. temperaturethen cooled
  2. additionpoured onto water (11 mL)
  3. extractionextracted with ethyl acetate (4×10 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue purified by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-d9106203de7a4564a9e158c62a38a050
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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