1,2-Dichloroethane → N,N-Di(propan-2-yl)-2-(pyridin-3-yl)acetamide

HRID 2059807Notes

Reaction equation

HRID 2059807 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=O)[CH:2]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[CH:25]([NH:28][CH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C>CN(C=O)C>[CH:25]([N:28]([CH:29]([CH3:31])[CH3:30])[C:8](=[O:10])[CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)([CH3:27])[CH3:26]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 1083-Pyridineacetic acidHCID 7912DiisopropylamineHCID 81531DiisopropylethylamineHCID 181649HOAt

Product 1

HCID 57429229N,N-Di(propan-2-yl)-2-(pyridin-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of pyridin-3-ylacetic acid (1.0 g, 7.292 mmol), EDC (2.796 g, 14.584 mmol) and HOAt (992 mg, 7.292 mmol) in 10 mL DMF were added diisopropyl amine (1.476 g, 14.584 mmol) and Hunig's base (1.885 g, 14.584 mmol). The reaction mixture was stirred at room temperature overnight and then partitioned between ether and half-saturated aq NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The resulting residue was purified by flash chromatography using a linear gradient of 0% to 6% MeOH—NH3 (90:10 v/v) in CH2Cl2 to give a white solid.

Workup

  1. custompartitioned between ether and half-saturated aq NaHCO3
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography
  6. customto give a white solid

Sources & evidence

ORD record
ord-9caa7c5c09604499a93bcbddca83b3ac
Source dataset
uspto-grants-2012_10
Patent number
US08278317B2

Reaction notes

Loading…