Sodium Bicarbonate → HCID 10223021, compound

HRID 2211673Notes

Reaction equation

HRID 2211673 reaction equation
C([N:4]1[C:9]2[CH:10]=[C:11]([NH:14][C:15](=[O:31])[C:16]3[CH:21]=[CH:20][CH:19]=[N:18][C:17]=3[NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH:12]=[CH:13][C:8]=2[O:7][C:6]([CH3:33])([CH3:32])[CH2:5]1)(=O)C.C([O-])(O)=O.[Na+]>CCO>[CH3:32][C:6]1([CH3:33])[CH2:5][NH:4][C:9]2[CH:10]=[C:11]([NH:14][C:15](=[O:31])[C:16]3[CH:21]=[CH:20][CH:19]=[N:18][C:17]=3[NH:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[CH:12]=[CH:13][C:8]=2[O:7]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 10182264HCID 10182264, compound

Product 1

HCID 10223021HCID 10223021, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

N-(4-Acetyl-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-2-(4-fluoro-benzylamino)-nicotinamide (250 mg, Example 52) was dissolved in EtOH (10 mL) and treated with conc. HCL (0.5 mL) at 60° C. for 16 h. The mixture was cooled to 0° C. and sat. NaHCO3 (aq) was added. The mixture was extracted with EtOAc (3×50 mL) and the combined organic fractions were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (50% EtOAc/hexanes). M+H 407.3; Calc'd for C23H23FN4O2: 406.18.

Workup

  1. additiontreated with conc. HCL (0.5 mL) at 60° C. for 16 h
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. washthe combined organic fractions were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0cff287f97184dba8fdf04f7ca85673a
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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