4-Aminopyridine → HCID 18349050, compound

HRID 2268569Notes

Reaction equation

HRID 2268569 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][C:9]([OH:11])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH2:58][C:59]1[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][C:9]([NH:58][C:59]1[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=1)=[O:11]

Participants

7

Reactant 5

HCID 17274-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18348951HCID 18348951, compound

Product 1

HCID 18349050HCID 18349050, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(5-bromo-3-methoxycarbonyl-phenoxy)-acetic acid (10.6 g), TBTU (19.3 g) and HOBt (5.1 g) in dry DMF (50 ml) was treated with DIPEA (9.9 ml). The resulting solution was stirred under a nitrogen atmosphere and was then treated with 4-aminopyridine (3.6 g) after 30 min. The resulting mixture was stirred for 18 h and then concentrated at reduced pressure to give a yellow viscous gum which was partitioned between ethyl acetate and water. The aqueous layer was removed and the organic phase washed with further water, 1M sodium hydroxide solution, aqueous saturated ammonium chloride, water and dried with brine and over sodium sulphate. The organic phase was concentrated under reduced pressure giving the title compound as a yellow solid (6.60 g).

Workup

  1. stirringThe resulting mixture was stirred for 18 h
  2. concentrationconcentrated at reduced pressure
  3. customto give a yellow viscous gum which
  4. customwas partitioned between ethyl acetate and water
  5. customThe aqueous layer was removed
  6. washthe organic phase washed with further water, 1M sodium hydroxide solution, aqueous saturated ammonium chloride, water
  7. dry with materialdried with brine and over sodium sulphate
  8. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6b9bb175c2640edba754e4f4b6ab6c1
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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