Sodium Hydroxide → HCID 178482647, compound

HRID 2114043Notes

Reaction equation

HRID 2114043 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]3[N:29]=[CH:30][NH:31][CH:32]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[NH:31]1[CH:32]=[C:28]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]([N:25]([CH3:27])[CH3:26])=[CH:23][CH:24]=4)[CH:18]=3)[NH:10][CH:11]=2)[N:29]=[CH:30]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178482645HCID 178482645, compound

Product 1

HCID 178482647HCID 178482647, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 17 (50 mg, 0.113 mmol) in EtOH (2.5 mL) was added 10% aq. NaOH (1.3 mL) and the reaction mixture was stirred at room temperature for 2 h then at 85° C. for 10 rain. It was cooled and poured onto water (3 mL) and extracted with ethyl acetate (4×5 mL). The combined organic extracts were dried (MgSO4) and concentrated. The residue was 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 product 18 as a white solid (9.0 mg, 26%); 1H NMR (400 MHz, CDCl3+4 drops CD3OD) δ 2.97 (s, 6H), 6.83 (d, J=8.9 Hz, 2H), 7.27 (d, J=1.0 Hz, 1H), 7.50 (d, J=8.8 Hz, 2H), 7.63 (s, 1H), 7.67 (d, J=1.0 Hz, 1H), 8.24 (d, J=2.1 Hz, 1H), 8.43 (d, J=2.0 Hz, 1H); MS (CI) m/z 304.1 (MH), 345.1 (M+MeCN).

Workup

  1. customat 85° C.
  2. temperatureIt was cooled
  3. additionpoured onto water (3 mL)
  4. extractionextracted with ethyl acetate (4×5 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-9aa1a085b15d447c9cf19dc7b738634b
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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