Dicyclohexylcarbodiimide → N-(2,3'-bipyridin-6'-yl)-2-(6-chloro-5-methylpyridin-3-yl)acetamide

HRID 592160Notes

Reaction equation

HRID 592160 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[CH3:12].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[N:21][C:22]([NH2:25])=[CH:23][CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[N:21][C:22]([NH:25][C:9](=[O:11])[CH2:8][C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[C:3]([CH3:12])[CH:4]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 124522625-(Pyridin-2-yl)pyridin-2-amineHCID 552673572-(6-Chloro-5-methylpyridin-3-yl)acetic acid

Product 1

HCID 58447789N-(2,3'-bipyridin-6'-yl)-2-(6-chloro-5-methylpyridin-3-yl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(6-chloro-5-methylpyridin-3-yl)acetic acid 74-4 (57 mg, 0.31 mmol), 2,3′-bipyridin-6′-amine 124-1 (51 mg, 0.30 mmol), 1,3-dicyclohexylcarbodiimide (75 mg, 0.36 mmol) and 4-(dimethylamino)pyridine (6 mg, 0.06 mmol) in DMF (1.2 mL) was stirred at room temperature for 10 hours. The reaction mixture was filtered through celite, washed and diluted with ethyl acetate (30 ml) and extracted with water 930 ml×2). The organic phase was dried over Na2SO4 and concentrated by evaporation. The residue was subjected to silica gel column chromatography with ethyl acetate as eluent to give N-(2,3′-bipyridin-6′-yl)-2-(6-chloro-5-methylpyridin-3-yl)acetamide 124-2 as white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed
  3. additiondiluted with ethyl acetate (30 ml)
  4. extractionextracted with water 930 ml×2)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5b5118c8ef60475dbd7261eecc047ec1
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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