Triethylamine → 2-Amino-N-(5-bromo-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide

HRID 1171231Notes

Reaction equation

HRID 1171231 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][NH2:11])=[CH:7][C:6]=2[CH:12]=1.[NH2:13][C:14]1[N:22]=[C:21]([CH2:23][O:24][CH3:25])[CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O.CN(C)C=O>[NH2:13][C:14]1[N:22]=[C:21]([CH2:23][O:24][CH3:25])[CH:20]=[CH:19][C:15]=1[C:16]([NH:11][CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:12][C:6]=2[CH:7]=1)=[O:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2795538(5-Bromobenzo[b]furan-2-yl)methylamineHCID 231304372-Amino-6-methoxymethylnicotinic acid

Product 1

HCID 576082252-Amino-N-(5-bromo-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamideYield 40.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To an N,N-dimethylformamide (10 mL) solution of C-(5-bromo-benzofuran-2-yl)-methylamine (455 mg, 2.01 mmol) described in Production Example 56-1-4 were added 2-amino-6-methoxymethyl-nicotinic acid (293 mg, 1.61 mmol) described in Production Example 4-1-5, triethylamine (700 μL, 5.03 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.07 g, 2.41 mmol) at room temperature, which was stirred for 12 hours. Water was added to the reaction solution at room temperature followed by extraction with ethyl acetate. The organic layer was washed with water and sat. NaCl followed by drying over anhydrous magnesium sulfate, filtering and concentrating the filtrate under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (255 mg, 33%) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationconcentrating the filtrate under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d8269bad9286466ebde3c8c72d0386d1
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

Loading…