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

HRID 1831509ノート

反応式

HRID 1831509 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-d8d355299af64dc99a40f3ebc1038783
出典データセット
uspto-grants-2006_06
特許番号
US07067658B2

反応ノート

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