p-Toluenesulfonic acid → 2-(5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)-3-phenethyl-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1170903ノート

反応式

HRID 1170903 の反応式
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9])=[C:6]([C:19]([F:22])([F:21])[F:20])[N:5]=[CH:4][CH:3]=1.[CH3:23][C:24]1[N:25]([C:30]2[S:34][CH:33]=[N:32][C:31]=2[CH:35]=O)[C:26]([CH3:29])=[CH:27][CH:28]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:23][C:24]1[N:25]([C:30]2[S:34][CH:33]=[N:32][C:31]=2[C:35]2[N:10]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:9])[C:7]3[C:6]([C:19]([F:22])([F:20])[F:21])=[N:5][CH:4]=[CH:3][C:2]=3[N:1]=2)[C:26]([CH3:29])=[CH:27][CH:28]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 595538795-(2,5-Dimethyl-1H-pyrrol-1-YL)thiazole-4-carbaldehydeHCID 595538854-amino-N-phenethyl-2-(trifluoromethyl)nicotinamide

生成物 1

HCID 595538992-(5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)-3-phenethyl-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one収率 17.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A solution of 4-amino-N-phenethyl-2-(trifluoromethyl)nicotinamide (25.5 mg, 0.082 mmol), 5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazole-4-carbaldehyde (17 mg, 0.082 mmol) and TsOH (1.4 mg, 0.008 mmol) in toluene was heated at reflux overnight. The reaction was then filtered and to the crude mixture was added manganese oxide. The reaction was heated at 110° C. for 4 h. The reaction mixture was filtered, concentrated and purified with silica gel chromatography providing a solid, 2-(5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)-3-phenethyl-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one (7 mg). 1H NMR (400 MHz, CDCl3) δ 9.02 (s, 1H), 8.76 (d, 1H), 7.69 (m, 1H), 7.51 (m, 1H), 7.48 (d, 1H), 7.32 (m, 5H), 4.20 (m, 2H), 3.32 (m, 2H), 2.07 (s, 6H). MS m/z 496.5 (M+H)+.

後処理

  1. temperatureat reflux overnight
  2. filtrationThe reaction was then filtered and to the crude mixture
  3. additionwas added manganese oxide
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated
  6. custompurified with silica gel chromatography

出典と根拠

ORDレコード
ord-0aa4247d58904a2a97ca5085ffd6de8b
出典データセット
uspto-grants-2010_11
特許番号
US07829572B2

反応ノート

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