4-(Morpholin-4-yl)benzene-1,2-diamine → 3-chloro-6'-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-[2,3]bipyridinyl-5-carboxylic acid methyl ester

HRID 2089123Notes

Reaction equation

HRID 2089123 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:19])[C:8]([C:11]2[CH:12]=[N:13][C:14]([CH:17]=O)=[CH:15][CH:16]=2)=[N:9][CH:10]=1)=[O:4].[O:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:27]=[C:28]([NH2:33])[C:29]([NH2:32])=[CH:30][CH:31]=2)[CH2:22][CH2:21]1>[N+](C1C=CC=CC=1)([O-])=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:19])[C:8]([C:11]2[CH:12]=[N:13][C:14]([C:17]3[NH:33][C:28]4[CH:27]=[C:26]([N:23]5[CH2:24][CH2:25][O:20][CH2:21][CH2:22]5)[CH:31]=[CH:30][C:29]=4[N:32]=3)=[CH:15][CH:16]=2)=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 141123324-(Morpholin-4-yl)benzene-1,2-diamineHCID 578256963-Chloro-6'-formyl-[2,3]bipyridyl-5-carboxylic acid methyl ester

Product 1

HCID 250601583-chloro-6'-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-[2,3]bipyridinyl-5-carboxylic acid methyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

0.50 g of 3-chloro-6′-formyl-[2,3′]bipyridyl-5-carboxylic acid methyl ester (13) (1.81 mmol) prepared in Example 9 and 0.35 g of 4-morpholinobenzene-1,2-diamine(18) (1.81 mmol) prepared in Example 12 were dissolved in nitrobenzene (5.0 mL), and refluxed under heating for 2 hours. The reactant was cooled to room temperature, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: ethyl acetate/hexane=1/1) to obtain 0.55 g of 3-chloro-6′-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-[2,3′]bipyridinyl-5-carboxylic acid methyl ester (yield 68%).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated by column chromatography (eluting solvent: ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-43954301b5c94e36ba3cfdbdc86172dc
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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