Citric Acid → HCID 17848361, compound

HRID 917610Notes

Reaction equation

HRID 917610 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([Cl:21])[CH:14]=2)=[N:9][C:8](Cl)=[CH:7][N:6]=1)=[O:4].[OH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.CC(C)([O-])C.[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([Cl:21])[CH:14]=2)=[N:9][C:8]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 11474PiconolHCID 22665590HCID 22665590, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 17848361HCID 17848361, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-methoxycarbonyl-3-(3-chloro-4-methoxybenzylamino)-5-chloropyrazine (prepared in the above Example 297(3)) 71 mg and 2-hydroxymethylpyridine 25 mg in tetrahydrofuran 3 ml is added potassium tert-butoxide 26 mg under ice cooling. The mixture is stirred for 30 minutes at the same temperature and diluted a 10% aqueous citric acid solution. The solution is extracted with ethyl acetate and the extract is washed with water and an aqueous saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue is purified and separated with silica gel chromatography (silica gel 5 g, solvent; chloroform:ethyl acetate=3:1) and crystallized from isopropyl ether to give 2-methoxycarbonyl-3-(3-chloro-4-methoxybenzylamino)-5-(2-pyridylmethoxy)pyrazine as a pale yellow crystalline powder, 25 mg. mp 132-133° C., MS(m/z): 415(M+H)+

Workup

  1. extractionThe solution is extracted with ethyl acetate
  2. washthe extract is washed with water
  3. dry with materialan aqueous saturated sodium chloride solution, dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified
  6. customseparated with silica gel chromatography (silica gel 5 g, solvent; chloroform:ethyl acetate=3:1)
  7. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-a2be140ce7f54df2a800fcdd61db837d
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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