Sodium Hydroxide → HCID 16064800, compound

HRID 1991116Notes

Reaction equation

HRID 1991116 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[C:13]3[C:12]([C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO.CCOC(C)=O.[Cl-].[Na+].O>[CH2:19]([C:17]1[CH:18]=[C:13]2[C:12]([C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59128684HCID 59128684, compound

Product 1

HCID 16064800HCID 16064800, compoundYield 73.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of benzyl derivative 38 (36 mg, 0.08 mmol) and 10% NaOH solution (0.80 mL) in EtOH (2.5 mL) was heated at 90° C. After 1 h the mixture was cooled to r.t., diluted with AcOEt and saturated brine and partitioned. The aqueous layer was extracted with AcOEt (3×). The combined organic extracts were dried (MgSO4), concentrated and the residue was purified by LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—MeCN (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 39 (17 mg, 70%). 1H NMR (400 MHz; CDCl3) δ 3.97 (s, 3H), 4.12 (s, 2H), 7.19-7.36 (m, 6H), 7.58 (s, 1H), 7.71 (s, 1H), 7.86 (brs, 1H), 8.24 (m, 1H), 8.79 (brs, 1H). MS (CI) m/z 289 (MH+).

Workup

  1. temperatureAfter 1 h the mixture was cooled to r.t.
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with AcOEt (3×)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified by LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-209e1fbb79604ee8a386f682e29921a5
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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