1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N'-[4-(Benzyloxy)phenyl]-2-chloropyridine-3-carbohydrazide

HRID 572165

Reaction equation

HRID 572165 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH2:26])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][NH:26][C:8]([C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:10])=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 762582-Chloronicotinic acidHCID 81531DiisopropylethylamineHCID 5613924-Benzyloxyphenylhydrazine

Product 1

HCID 86704974N'-[4-(Benzyloxy)phenyl]-2-chloropyridine-3-carbohydrazideYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloropyridine-3-carboxylic acid (3.30 g) in DMF (50 ml) were added [4-(benzyloxy)phenyl]hydrazine (5.0 g), HOBt (3.7 g), EDCI (4.6 g) and diisopropylethylamine (9.0 g), and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (5.0 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bfd42e8e04b5403f81fb3b812034444f
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Linked notes

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