Cyclopentanol → HCID 57968786, compound

HRID 1483684Notes

Reaction equation

HRID 1483684 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:10]1[N:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13]>CN(C=O)C>[Cl:19][C:17]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[C:10]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:18]=1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 221427782,6-Dichloropyridine-3-carboxamide

Product 1

HCID 57968786HCID 57968786, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of cyclopentanol (1.42 mL, 15.70 mmol) in DMF (5 mL) at 0° C. was added sodium hydride (95% in mineral oil, 0.39 g, 15.70 mmol) in portions and stirred for 1 h at room temperature. This mixture was slowly added to a solution of 2,6-dichloro-nicotinamide (2.0 g, 10.47 mmol) in DMF (10 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. DMF was removed under reduced pressure, and the resulting mixture was diluted with EtOAc (100 mL), washed with water (2×25 mL) and brine (2×25 mL) solution, dried over anhyd. Na2SO4, filtered, and concentrated to give yellow oil, which was purified by flash chromatography on silica gel using 10-25% EtOAc/hexanes as eluent to yield the title compound (1.94 g, 51%) as a transparent oil. 1H NMR (400 MHz, CDCl3) δ 8.44 (d, J=7.8 Hz, 1H), 7.65 (br. s., 1H), 7.03 (d, J=8.2 Hz, 1H), 5.74 (br. s., 1H), 5.70-5.57 (m, 1H), 2.25-1.95 (m, 2H), 1.90-1.66 (m, 6H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customDMF was removed under reduced pressure
  3. additionthe resulting mixture was diluted with EtOAc (100 mL)
  4. washwashed with water (2×25 mL) and brine (2×25 mL) solution
  5. customdried over anhyd
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated
  8. customto give yellow oil, which
  9. customwas purified by flash chromatography on silica gel using 10-25% EtOAc/hexanes as eluent

Sources & evidence

ORD record
ord-c0edb008ef484ac680b02cd56d0d0eec
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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