Ethanol → N-[3,5-bis(trifluoromethyl)phenyl]-4-{3-[(pyridin-4-ylmethyl)oxy]pyridin-2-yl}piperazine-1-carboxamide

HRID 907573ノート

反応式

HRID 907573 の反応式
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([C:28]#CC4C=CN=CC=4)=N[CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:38]([OH:40])[CH3:39]>[Pd]>[F:1][C:2]([F:36])([F:37])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([O:40][CH2:38][C:39]4[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=4)=[CH:28][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

参加物

4

反応物 2

HCID 702EthanolHCID 590139503'-Pyridin-4-ylethynyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide

生成物 1

HCID 10436864N-[3,5-bis(trifluoromethyl)phenyl]-4-{3-[(pyridin-4-ylmethyl)oxy]pyridin-2-yl}piperazine-1-carboxamide

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

3′-Pyridin-4-ylethynyl-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethylphenyl)amide (˜0.4 mmol) was dissolved in 5 mL ethanol. Then, 50 mg of 10% palladium on carbon was added. The reaction flask was flushed with hydrogen and the reaction was stirred at room temperature for 5 hr under 1 atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated under vacuum. The residue was purified by reverse phase HPLC to give N-[3,5-bis(trifluoromethyl)phenyl]-4-{3-[(pyridin-4-ylmethyl)oxy]pyridin-2-yl}piperazine-1-carboxamide (80 mg) as a yellow solid. 1H NMR (DMSO-d6) δ 9.34 (s, 1H), 8.48 (d, 2H), 8.23 (s, 1H), 8.20 (d, 1H), 8.14 (d, 2H), 7.58 (s, 1H), 7.39 (d, 2H), 3.66 (m, 4H), 3.13-3.43 (m, 8H) ppm.

後処理

  1. customThe reaction flask was flushed with hydrogen
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-fd875057d89b4ba0a405e5f7874fde0b
出典データセット
uspto-grants-2011_09
特許番号
US08013156B2

反応ノート

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