2-Aminopyridine → 2-(4-(2-tert-butylphenyl)piperazin-1-yl)-2-oxo-N-(pyridin-2-yl)acetamide

HRID 534908Notes

Reaction equation

HRID 534908 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:21])[C:18](O)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:21])[C:18]([NH:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=2)=[O:19])[CH2:15][CH2:16]1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 667508542-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

Product 1

HCID 667927642-(4-(2-tert-butylphenyl)piperazin-1-yl)-2-oxo-N-(pyridin-2-yl)acetamideYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-(2-tert-butylphenyl)piperazin-1-yl)-2-oxo-acetic acid (0.086 g, 0.30 mmol) in methylene chloride (4.0 mL) was added EDCI (0.75 g, 0.39 mmol) and HOBt (0.053 g, 0.39 mmol) at room temperature. After 30 min 2-aminopyridine (0.031 g, 0.33 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. After this time, the reaction mixture was concentrated under reduced pressure and the residue purified by flash column chromatography (silica gel, 80:20 heptane/ethyl acetate) to provided 2-(4-(2-tert-butylphenyl)piperazin-1-yl)-2-oxo-N-(pyridin-2-yl)acetamide (0.043 g, 39%) as a white solid, mp 168-172° C.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by flash column chromatography (silica gel, 80:20 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-e8395afd88cf438b9bdcc3e9b7b7d36b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…