4-Aminopyridine → HCID 23499488, compound

HRID 1836335Notes

Reaction equation

HRID 1836335 reaction equation
[CH2:1]([S:8]([NH:11][NH:12][C:13]1[C:14](=[O:24])[N:15]([CH2:20][CH2:21][CH2:22]Br)[C:16]([CH3:19])=[CH:17][N:18]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.N1C(C)=CC=CC=1C>O1CCOCC1>[CH2:1]([S:8]([NH:11][NH:12][C:13]1[C:14](=[O:24])[N:15]([CH2:20][CH2:21][CH2:22][C:28]2[CH:27]=[C:26]([NH2:25])[CH:31]=[CH:30][N:29]=2)[C:16]([CH3:19])=[CH:17][N:18]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 79372,6-LutidineHCID 23499507HCID 23499507, compound2×

Product 1

HCID 23499488HCID 23499488, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-(2-benzylsulfonylhydrazino)-1-(3-bromopropyl)-6-methylpyrazinone, the product of Example 32, (0.174 g, 0.42 mmol) in dioxane (15 mL), are added 4-aminopyridine (0.048 g, 0.51 mmol) and 2,6-lutidine (0.099 mL, 0.85 mmol). The resulting mixture is stirred at 90° C. for about 15 hours and then is concentrated under reduced pressure. The crude residue is purified by RP-HPLC using acetonitrile/water/trifluoroacetic acid as eluent to afford the title compound.

Workup

  1. concentrationis concentrated under reduced pressure
  2. customThe crude residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-55a61750c8a74f5390dda35c467a172e
Source dataset
uspto-grants-2004_08
Patent number
US06777431B2

Reaction notes

Loading…