Acetate → HCID 178491348, compound

HRID 929675Notes

Reaction equation

HRID 929675 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:4]=1[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][N:11]=1)=[NH:8].[Br-].[CH2:24]([Zn+])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])(=O)C>[Pd]>[CH2:24]([C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]2[C:3]([O:2][CH3:1])=[CH:20][CH:19]=[CH:18][C:17]=2[O:21][CH3:22])=[NH:8])=[N:11][CH:12]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 175AcetateHCID 178419772HCID 178419772, compound2×HCID 178491352N-(2,6-dimethoxybenzyl)-N'-(5-iodopyridin-2-yl)guanidine

Product 1

HCID 178491348HCID 178491348, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The preparation was carried out analogously to Example 67, using 0.200 g (0.485 mmol) N-(2,6-dimethoxybenzyl)-N′-(5-iodopyridin-2-yl)guanidine and 2.43 mL (1.213 mmol) of the benzyl zinc bromide solution (0.5 M in tetrahydrofuran) under Pd catalysis with 20 mg (0.055 mmol) [1,1-bis-(diphenylphosphino)ferrocene]palladium(II) chloride-methylene chloride. The mixture was likewise heated under a nitrogen atmosphere, first under reflux for 6 hr, and then after repeated additions of 2×2.43 mL (1.213 mmol) of the 0.5 M benzyl zinc bromide solution and the same quantity of Pd catalyst for an additional 6 hr and 4 hr, respectively, for a total of 16 hr of heating. After appropriate workup and purification via preparative HPLC (Merck Chromolith RP-18 100×25 mm, eluent: water/acetonitrile/0.1 M acetic acid), 48 mg (0.109 mmol, 23%) pure N-(5-benzylpyridin-2-yl)-N′-(2,6-dimethoxybenzyl)guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1).

Workup

  1. temperatureThe mixture was likewise heated under a nitrogen atmosphere
  2. temperaturefirst under reflux for 6 hr
  3. temperature4 hr, respectively, for a total of 16 hr of heating
  4. customAfter appropriate workup and purification via preparative HPLC (Merck Chromolith RP-18 100×25 mm, eluent: water/acetonitrile/0.1 M acetic acid)

Sources & evidence

ORD record
ord-89f64a8ae5aa42bba4d7f8aa4a797cd2
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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