Ethyl 3,3,3-trifluoro-2-oxopropanoate → Tert-butyl 4-(3-oxo-2-(trifluoromethyl)-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)naphthalen-1-ylcarbamate

HRID 1749070ノート

反応式

HRID 1749070 の反応式
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[F:28][C:29]([F:38])([F:37])[C:30](=O)[C:31](OCC)=[O:32]>C(O)C>[O:32]=[C:31]1[NH:1][C:2]2[N:3]=[CH:4][CH:5]=[C:6]([O:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[CH:12][CH:11]=3)[C:7]=2[N:8]=[C:30]1[C:29]([F:38])([F:37])[F:28]

参加物

4

反応物 2

HCID 2737239Ethyl 3,3,3-trifluoro-2-oxopropanoateHCID 44186229Tert-butyl 4-(2,3-diaminopyridin-4-yloxy)naphthalen-1-ylcarbamate

生成物 1

HCID 46900749Tert-butyl 4-(3-oxo-2-(trifluoromethyl)-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)naphthalen-1-ylcarbamate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To tert-butyl 4-(2,3-diaminopyridin-4-yloxy)naphthalen-1-ylcarbamate (1.00 g, 2.73 mmol) dissolved in 20 mL of anhydrous ethanol under argon and at reflux was added the ethyl trifluoropyruvate (697 mg, 0.50 mL, 4.10 mmol). The reaction mixture was stirred at reflux for 3 hours. After cooling at RT, a precipitate was formed, filtered off and rinsed with Et2O. tert-butyl 4-(3-oxo-2-(trifluoromethyl)-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)naphthalen-1-ylcarbamate was obtained as a white solid (116 mg, 0.246 mmol, 9%). The filtrate was evaporated under vacuum. The residue was chromatographied (eluent: CH2Cl2/EtOAc: 4/1 towards 0/1) to afford the second isomer as a slightly yellow solid (540 mg, 1.14 mmol, 42%).

後処理

  1. temperatureat reflux
  2. temperatureat reflux for 3 hours
  3. customa precipitate was formed
  4. filtrationfiltered off
  5. washrinsed with Et2O

出典と根拠

ORDレコード
ord-a3de033e9846403c98f36492057ebdf3
出典データセット
uspto-grants-2015_10
特許番号
US09155737B2

反応ノート

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