Methyl 5-chloropyrazine-2-carboxylate → 5-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid methyl ester

HRID 1435837Notes

Reaction equation

HRID 1435837 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][NH2:14].[CH3:15][O:16][C:17]([C:19]1[CH:24]=[N:23][C:22](Cl)=[CH:21][N:20]=1)=[O:18]>CS(C)=O>[CH3:15][O:16][C:17]([C:19]1[CH:24]=[N:23][C:22]([NH:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:21][N:20]=1)=[O:18]

Participants

4

Reactant 2

HCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 2776151(5-Methyl-3-phenyl-4-isoxazolyl)methylamine

Product 1

HCID 684456305-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (5-methyl-3-phenyl-4-isoxazolyl)methylamine (2.4 g, 12.7 mmol) and 5-chloro-pyrazine-2-carboxylic acid methyl ester (2.2 g, 12.7 mmol) in DMSO (15 mL) was heated with microwave irradiation to 160° C. for 30 min. After cooling to room temperature the reaction mixture was extracted (ethyl acetate/water). The organic phase was dried over sodium sulfate, concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 20:80). The oily product obtained was triturated with diisopropylether and ethyl acetate to afford the title compound (3.5 g, 84% as an off-white solid. MS: m/e=325.4 [M+H]+.

Workup

  1. extractionwas extracted (ethyl acetate/water)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customchromatographed (SiO2, heptane:ethyl acetate=100:0 to 20:80)
  5. customThe oily product obtained
  6. customwas triturated with diisopropylether and ethyl acetate

Sources & evidence

ORD record
ord-7742b91250b94516800cbbc043c2e795
Source dataset
uspto-grants-2009_11
Patent number
US07618973B2

Reaction notes

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