5-Hydroxy-2-pentanone → 6-Chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinamide

HRID 2284503

Reaction equation

HRID 2284503 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20].[H-].[Na+]>CN(C=O)C>[Cl:11][C:9]1[C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([O:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[N:10]=1

Participants

5

Reactant 3

HCID 140665-Hydroxy-2-pentanoneHCID 24758Sodium hydrideHCID 866617192,6-Dichloro-5-cyclopropylnicotinamide

Product 1

HCID 866617286-Chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinamideYield 19.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,6-dichloro-5-cyclopropylnicotinamide (2.00 g, 8.66 mmol) and 5-hydroxypentan-2-one (883 mg, 8.66 mmol) in DMF (30 mL) was added and NaH (416 mg, 10.4 mmol) in portions at 0° C. The mixture was stirred at r.t. overnight, quenched by water, extracted by EtOAc. The separated organics was dried, concentrated and purified by column chromatography (Petroleum ether:EtOAc=10:1-1:1) to give 6-chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinamide (500 mg, 19.4%).

Workup

  1. additionwas added
  2. customat 0° C
  3. customquenched by water
  4. extractionextracted by EtOAc
  5. customThe separated organics was dried
  6. concentrationconcentrated
  7. custompurified by column chromatography (Petroleum ether:EtOAc=10:1-1:1)

Sources & evidence

ORD record
ord-c320b779add54b019cd7c26d7e3b13d0
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Linked notes

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