Methyl pyruvate → 8-(2,4-dichloro-phenyl)-4-(2-methoxy-1-methyl-ethyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one

HRID 1831509노트

반응식

HRID 1831509 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH3:20])[CH2:17][O:18][CH3:19])[C:10]=1[NH2:21].[C:22](OC)(=[O:26])[C:23]([CH3:25])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:21]=[C:23]([CH3:25])[C:22](=[O:26])[N:15]([CH:16]([CH3:20])[CH2:17][O:18][CH3:19])[C:11]=2[N:12]=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 11748Methyl pyruvateHCID 627056514-(2,4-dichloro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine

생성물 1

HCID 220520698-(2,4-dichloro-phenyl)-4-(2-methoxy-1-methyl-ethyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one수율 2.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

4-(2,4-Dichloro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine (0.13 g, 0.40 mmol) was dissolved in toluene (20 mL), followed by methyl pyruvate (0.081 g, 0.80 mmol) and heated at reflux overnight. The reaction was concentrated in vacuo and purified by reverse phase prep HPLC to yield 3.2 mg (2%) of 8-(2,4-dichloro-phenyl)-4-(2-methoxy-1-methyl-ethyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 9): 1H NMR (300 MHz, CD3OD): δ 8.6 (d, 1H), 7.6 (s, 1H), 7.4–7.25 (m, 3H), 4.4 (m, 1H). 3.8 (m, 1H), 3.3 (s, 3H), 2.4 (s, 3H), 1.6 (d, 2H), 1.25 (s, 2H). MS (AP) m/z 378.3 [(M+H)+, 100].

후처리

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified by reverse phase prep HPLC

출처 및 근거

ORD 기록
ord-d8d355299af64dc99a40f3ebc1038783
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067658B2

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