4-Aminopyridine → HCID 18348915, compound

HRID 2268564Notes

Reaction equation

HRID 2268564 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([CH3:14])[CH:13]=1)[O:6][CH2:7][C:8]([OH:10])=O)=[O:2].[NH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([CH3:14])[CH:13]=1)[O:6][CH2:7][C:8]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[O:10])=[O:2]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18348865HCID 18348865, compound

Product 1

HCID 18348915HCID 18348915, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3-Formyl-5-methyl-phenoxy)-acetic acid (0.47 g) and 4-aminopyridine (0.46 g) were dissolved in dry DMF (10 ml). The resulting solution, stirring under a nitrogen atmosphere, was treated with TBTU (0.82 g). The resulting mixture was stirred for 68 h and then concentrated at reduced pressure to give a yellow viscous gum. This crude material was purified by preparative hplc. The purified product was partitioned between ethyl acetate and an aqueous solution saturated with sodium bicarbonate, sodium chloride and ammonium sulphate. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure giving the title compound as an off-white solid (0.40 g).

Workup

  1. stirringThe resulting mixture was stirred for 68 h
  2. concentrationconcentrated at reduced pressure
  3. customto give a yellow viscous gum
  4. customThis crude material was purified by preparative hplc
  5. customThe purified product was partitioned between ethyl acetate
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e9e6181139d44d588c6528e4ede37b65
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

Loading…