Ethylamine → 3-chloro-6'-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-[2,3']bipyridinyl-5-carboxylic acid ethyl amide

HRID 1430107Notes

Reaction equation

HRID 1430107 reaction equation
[Cl:1][C:2]1[C:3]([C:11]2[CH:12]=[N:13][C:14]([C:17]3[NH:21][C:20]4[CH:22]=[C:23]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)[CH:24]=[CH:25][C:19]=4[N:18]=3)=[CH:15][CH:16]=2)=[N:4][CH:5]=[C:6]([C:8](O)=[O:9])[CH:7]=1.[CH2:32]([NH2:34])[CH3:33]>O1CCCC1.CN(C)C=O>[CH2:32]([NH:34][C:8]([C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([C:11]2[CH:12]=[N:13][C:14]([C:17]3[NH:21][C:20]4[CH:22]=[C:23]([N:26]5[CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)[CH:24]=[CH:25][C:19]=4[N:18]=3)=[CH:15][CH:16]=2)=[N:4][CH:5]=1)=[O:9])[CH3:33]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 250604343-chloro-6'-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-[2,3]bipyridinyl-5-carboxylic acid

Product 1

HCID 250611973-chloro-6'-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-[2,3']bipyridinyl-5-carboxylic acid ethyl amideYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.43 g of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphine (1.12 mmol) was added to 0.49 g of 3-chloro-6′-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-[2,3]bipyridinyl-5-carboxylic acid (79) (1.12 mmol) prepared in Example 66 dissolved in 1.0 mL of tetrahydrofuran and 1.0 mL of dimethylformamide, and stirred at room temperature for 10 minutes. 0.56 mL of ethylamine (1.12 mmol) in 2.0 M tetrahydrofuran solution was added thereto, and refluxed under heating and stirring for 18 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. Then, the mixture was dissolved in ethyl acetate, and washed with water. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=20/1) to obtain 0.35 g of 3-chloro-6′-(6-morpholin-4-yl-1H-benzoimidazol-2-yl)-[2,3]bipyridinyl-5-carboxylic acid ethyl amide (yield 68%).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThen, the mixture was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was separated by column chromatography (eluting solvent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-42ee8aed380646af8614b0bc7a4aa3a6
Source dataset
uspto-grants-2015_01
Patent number
US08940769B2

Reaction notes

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