Water → HCID 57608234, compound

HRID 1171213Notes

Reaction equation

HRID 1171213 reaction equation
[NH2:1][C:2]1[N:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([O:17]CC3C=CC=CC=3)[CH:14]=[CH:13][C:11]=2[CH:12]=1)=[O:5].C(=O)(O)[O-].[Na+].O>FC(F)(F)C(O)=O>[NH2:1][C:2]1[N:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:11]=2[CH:12]=1)=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 57608272HCID 57608272, compound

Product 1

HCID 57608234HCID 57608234, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a trifluoroacetic acid solvent of 2-amino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-nicotinamide (323 mg, 865 mmol) described in Example 58 at 0° C., which was stirred at room temperature for 3 hours. Sodium bicarbonate and water were added to the reaction solution at 0° C. followed by extraction with ethyl acetate. The organic layer was washed with sat. NaCl followed by drying by adding anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (219 mg, 89%) as a white solid.

Workup

  1. customdescribed in Example 58 at 0° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with sat. NaCl
  4. customby drying
  5. additionby adding anhydrous magnesium sulfate
  6. filtrationfiltering
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-74f825e54c3e41bea3c9e64696847e5b
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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