3-Pyridinemethanol → HCID 86598525, compound

HRID 1727258Notes

Reaction equation

HRID 1727258 reaction equation
C1N=CN([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])C=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=1.NCC1[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=1.C(N(CC)CC)C>C1COCC1>[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][C:6](=[O:7])[NH:8][CH2:9][C:10]2[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 75103-PyridinemethanolHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 6496943[4-(Aminomethyl)phenyl]methanol

Product 1

HCID 86598525HCID 86598525, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of N,N-carbonyldiimidazole (2.1 g, 12.8 mmol) in THF (15 mL) was added a solution of 3-pyridylcarbinol (1.3 g, 11.6 mmol) in THF (15 mL). After stirring for 30 minutes, a solution of (4-aminomethylphenyl)methanol (1.4 g, 10.4 mmol) in THF (15 mL) and triethylamine (3.2 mL, 23.2 mmol) were added, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water (30 mL) and extracted with 10% MeOH in CHCl3 (30 mL×2). The organic layer was dried (Na2SO4), evaporated under reduced pressure, and the residue was purified by MPLC on silica gel (5% MeOH in CHCl3) to afford the titled compound (1.31 g, 46%) as a white solid.

Workup

  1. stirringthe mixture was stirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with water (30 mL)
  4. extractionextracted with 10% MeOH in CHCl3 (30 mL×2)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customthe residue was purified by MPLC on silica gel (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-8f4a23b049d140ca83c8b5663ddc9721
Source dataset
uspto-grants-2009_02
Patent number
US07495022B2

Reaction notes

Loading…