6-Methylnicotinic acid → HCID 16792175, compound

HRID 2069087Notes

Reaction equation

HRID 2069087 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7]C(=O)OCC2C=CC=CC=2)[CH2:3][CH2:2]1.[CH3:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][N:20]=1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[NH2:7][CH:4]1[CH2:3][CH2:2][N:1]([C:23]([C:22]2[CH:21]=[N:20][C:19]([CH3:18])=[CH:27][CH:26]=2)=[O:24])[CH2:6][CH2:5]1

Participants

8

Reactant 5

HCID 1378606-Methylnicotinic acidHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 15143044-Cbz-aminopiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 16792175HCID 16792175, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (14 mL; WAKO) was added to a dichloromethane (98 mL) solution of Benzyl piperidin-4-ylcarbamate (5.33 g), 6-methylnicotinic acid (which may be referred to as sco100; 4.0 g; Ald), HOAt (4.0 g; Wata) and WSC.HCl (5.7 g; Wata) and the resulting mixture was stirred overnight at room temperature. Saturated sodium hydrogencarbonate solution (50 mL) was added to the reaction mixture solution, the resulting mixture was extracted, the organic layer was dried, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen; chloroform/methanol). Palladium carbon (10% by weight, Pe-type, 3.45 g; NECHEM) was added to a methanol (90 mL) solution of this product under a nitrogen atmosphere. The atmosphere in a reaction vessel was replaced with hydrogen at room temperature, the resulting mixture was stirred overnight, the atmosphere in the reaction vessel was returned to a nitrogen atmosphere, the residue was removed by filtration, the solvent was evaporated under reduced pressure, and the residue was dried to give the title compound (4.05 g).

Workup

  1. extractionthe resulting mixture was extracted
  2. customthe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (Yamazen; chloroform/methanol)
  5. additionPalladium carbon (10% by weight, Pe-type, 3.45 g; NECHEM) was added to a methanol (90 mL) solution of this product under a nitrogen atmosphere
  6. customThe atmosphere in a reaction vessel was replaced with hydrogen at room temperature
  7. stirringthe resulting mixture was stirred overnight
  8. customthe residue was removed by filtration
  9. customthe solvent was evaporated under reduced pressure
  10. customthe residue was dried

Sources & evidence

ORD record
ord-8a73eef89add4104a24dff95f49d183d
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

Loading…