Trifluoroacetic acid → 2,6-Diamino-N-(6-hydroxy-benzofuran-2-ylmethyl)-nicotinamide

HRID 1171190Notes

Reaction equation

HRID 1171190 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:10]=1[C:11]([NH:13][CH2:14][C:15]1[O:16][C:17]2[CH:23]=[C:22]([O:24]CC3C=CC=CC=3)[CH:21]=[CH:20][C:18]=2[CH:19]=1)=[O:12].C1(SC)C=CC=CC=1.C(=O)(O)[O-].[Na+]>O>[NH2:8][C:9]1[N:35]=[C:34]([NH2:36])[CH:33]=[CH:32][C:10]=1[C:11]([NH:13][CH2:14][C:15]1[O:16][C:17]2[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:18]=2[CH:19]=1)=[O:12]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 516892Sodium BicarbonateHCID 119608292,6-Diamino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-nicotinamide

Product 1

HCID 576082112,6-Diamino-N-(6-hydroxy-benzofuran-2-ylmethyl)-nicotinamideYield 55.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a trifluoroacetic acid (5 mL) solution of 2,6-diamino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-nicotinamide (238 mg, 612 μmol) described in Example 1 was added thioanisole (287 μL, 2.45 mmol) at 0° C., which was stirred at room temperature for 2 hours. To the reaction solution were added sodium bicarbonate and water at 0° C., followed by extraction with ethyl acetate. After washing the organic layer with sat. NaCl, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (101 mg, 55%) as a pale brown solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washAfter washing the organic layer with sat. NaCl
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-dcfedd61cc234ddcba90b5f6e50fef63
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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