Toluene → HCID 22665590, compound

HRID 917609Notes

Reaction equation

HRID 917609 reaction equation
CO[C:3]1[C:8]([Cl:9])=[N:7][C:6](Cl)=[C:5]([C:11]([OH:13])=[O:12])[N:4]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:18][NH2:19].[CH2:25](N(CC)CC)C.C1(C)C=CC=CC=1>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:25][O:13][C:11]([C:5]1[C:6]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:15]([Cl:14])[CH:16]=2)=[N:7][C:8]([Cl:9])=[CH:3][N:4]=1)=[O:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 17848356HCID 17848356, compound

Product 1

HCID 22665590HCID 22665590, compound

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Procedure

A mixture of 2-methoxycarboxy-3,5-dichloropyrazine (prepared in the above (2)) 234 mg, 3-chloro-4-methoxybenzylamine 204 mg, triethylamine 0.17 ml and anhydrous toluene 3 ml is stirred for 7 hours at room temperature. The reaction mixture is diluted with a 10% aqueous citric acid solution and the solution is extracted with ethyl acetate. 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 mg, solvent; hexane:chloroform=1:1) and then the desired fraction is concentrated in vacuo to give 2-methoxycarbonyl-3-(3-chloro-4-methoxybenzylamino)-5-chloropyrazine as a pale yellow crystalline powder 102 mg. mp 149-151° C., MS(m/z): 342(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 mg, solvent; hexane:chloroform=1:1)
  7. concentrationthe desired fraction is concentrated in vacuo

Sources & evidence

ORD record
ord-c1d0a01f527a4436a66c42607aad7f7f
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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