Reaction #41788

ord-2a8c737cc7894a259fe7b309a3c7403d

Reaction equation

CCc1cccc(Nc2nc3cc(Oc4ccnc(C(=O)NC)c4)ccc3n2C)c1
4-[2-(3-Ethyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid methylamide
[N-]=[N+]=NCc1ccccc1
benzyl azide
O=C1O[C@H]([C@@H](O)CO)C([O-])=C1O.[Na+]
sodium ascorbate
→
CNC(=O)c1cc(Oc2ccc3c(c2)nc(Nc2cccc(-c4cn(Cc5ccccc5)nn4)c2)n3C)ccn1
4-{2-(3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-phenyl amino]-1-methyl-1H-benzoimidazol-5-yloxy}-pyridine-2-carboxylic acid methyl amide

Reactants

CCc1cccc(Nc2nc3cc(Oc4ccnc(C(=O)NC)c4)ccc3n2C)c1
4-[2-(3-Ethyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid methylamide
[N-]=[N+]=NCc1ccccc1
benzyl azide
O=C1O[C@H]([C@@H](O)CO)C([O-])=C1O.[Na+]
sodium ascorbate

Reagents

O.O.O.O.O.O=S(=O)([O-])[O-].[Cu+2]
copper (II) sulfate pentahydrate

Solvents

CC(C)(C)O
t-butanol
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherprepared
  2. 2
    Filtrationthe solid collect via suction filtration

Procedure

To a mixture of 4-[2-(3-Ethyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid methylamide (1 eq) (prepared using previously described example 2), benzyl azide (1 eq) in t-butanol (0.1M) was added sodium ascorbate (0.05 eq), and copper (II) sulfate pentahydrate (0.01 eq). The resulting mixture was allowed to stir for 1 hour at room temperature. The mixture was then diluted with water and the solid collect via suction filtration. MS: MH+ 531

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728010B2uspto-grants-2010_06