Sodium Hydroxide → HCID 10354688, compound

HRID 2114052Notes

Reaction equation

HRID 2114052 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:23]=[CH:22][N:21]([Si](C(C)C)(C(C)C)C(C)C)[CH:20]=4)[CH:18]=[C:13]3[C:12]([C:34]3[CH:38]=[CH:37][O:36][CH:35]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>CCO>[O:36]1[CH:37]=[CH:38][C:34]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([C:19]4[CH:23]=[CH:22][NH:21][CH:20]=4)[CH:18]=3)[NH:10][CH:11]=2)=[CH:35]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 67051485HCID 67051485, compound

Product 1

HCID 10354688HCID 10354688, compoundYield 5,946%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 31 (15.3 mg, 0.28 μmol), EtOH (1.0 mL) and 10% aq. NaOH (0.5 mL) were heated at 110° C. for 40 min then cooled and poured onto saturated aqueous NaHCO3 (5 mL) and extracted with ethyl acetate (4×10 mL). The combined organic extracts were dried (MgSO4), concentrated and the residue purified by PTLC using 5% MeOH in CH2Cl2 to give the pure product as a solid (4.15 mg, 59%); 1H NMR (400 MHz, CDCl3) δ 6.60 (d, J=1.6 Hz, 1H), 6.72 (s, 1H), 6.92 (dd, J=4.7, 2.5 Hz, 1H), 7.15 (d, J=2.0 Hz, 1H), 7.41 (d, J=2.3 Hz, 1H), 7.54 (s, 1H), 7.82 (s, 1H), 8.15 (d, J=1.7 Hz, 1H), 8.37 (bs, NH), 8.57 (d, J=1.8 Hz, 1H), 8.96 (bs, NH).

Workup

  1. temperaturethen cooled
  2. extractionextracted with ethyl acetate (4×10 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customthe residue purified by PTLC

Sources & evidence

ORD record
ord-d84a25a4a47249d4a159cdfe598ad23d
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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