Pyridine → HCID 67283491, compound

HRID 1183154Notes

Reaction equation

HRID 1183154 reaction equation
N1C=CC=CC=1.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]([NH2:16])[CH3:15])[CH:8]=1.[CH:17]1([CH3:29])[CH2:22][CH2:21][CH:20]([CH:23]([CH3:25])[CH3:24])[CH:19]([C:26](Cl)=[O:27])[CH2:18]1>O1CCCC1>[CH:23]([C@@H:20]1[CH2:21][CH2:22][C@@H:17]([CH3:29])[CH2:18][C@H:19]1[C:26]([NH:16][CH:14]([CH3:15])[CH2:13][C:9]1[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=1)=[O:27])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 47124581-(pyridin-3-yl)propan-2-amineHCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Product 1

HCID 67283491HCID 67283491, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 25 mL round bottom flask, fitted with magnetic stirrer, 15 mL of tetrahydrofuran, 1.5 mmol (1.5 eq.) of pyridine and 1.1 mmol (1.1 eq.) of 1-(pyridin-3-yl)propan-2-amine were added. p-Menthane carboxylic acid chloride (1.0 mmol) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was extracted with MTBE and NaOH (1N in water). The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography, obtaining 220 mg of a white solid, mp 108-110° C.

Workup

  1. customIn a 25 mL round bottom flask, fitted with magnetic stirrer
  2. extractionThe reaction mixture was extracted with MTBE and NaOH (1N in water)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-419ae74c17e9471e91839e5317539306
Source dataset
uspto-grants-2014_03
Patent number
US08664261B2

Reaction notes

Loading…