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

HRID 600482노트

반응식

HRID 600482 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 684456305-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid methyl ester수율 85%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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 with ethyl acetate, and the combined extracts were washed with 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]+.

후처리

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

출처 및 근거

ORD 기록
ord-bc7b10695aa54050a76b60b340088ad2
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902201B2

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