Sodium Hydroxide → 5-[(2-Fluorophenyl)amino]-N-[4-(4-isopropylpiperazin-1-yl)phenyl]-1,3,4-oxadiazole-2-carboxamide

HRID 1713729ノート

反応式

HRID 1713729 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([O:16]CC)=O)=[N:11][N:10]=1.[OH-].[Na+].[CH:21]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)([CH3:23])[CH3:22].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>O.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:36][C:33]2[CH:32]=[CH:31][C:30]([N:27]3[CH2:26][CH2:25][N:24]([CH:21]([CH3:23])[CH3:22])[CH2:29][CH2:28]3)=[CH:35][CH:34]=2)=[O:16])=[N:11][N:10]=1

参加物

8

反応物 5

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 91615454-[4-(Propan-2-yl)piperazin-1-yl]anilineHCID 59464107Ethyl 5-[(2-fluorophenyl)amino]-1,3,4-oxadiazole-2-carboxylate2 回

生成物 1

HCID 117045275-[(2-Fluorophenyl)amino]-N-[4-(4-isopropylpiperazin-1-yl)phenyl]-1,3,4-oxadiazole-2-carboxamide収率 44%

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 6228Dimethylformamide溶媒2 回

実験手順

Ethyl 5-[(2-fluorophenyl)amino]-1,3,4-oxadiazole-2-carboxylate (Intermediate 40, 94 mg, 0.37 mmol) was stirred in water (1 mL). Sodium hydroxide (37 mg, 0.925 mmol) was dissolved in water (0.5 mL) and added to the reaction mixture. After stirring for 1 h the reaction was concentrated in vacuo to give a yellow solid which was dissolved in DMF (1 mL). [4-(4-Isopropylpiperazin-1-yl)phenyl]amine (WO02/057261) (89 mg, 0.41 mmol) dissolved in DMF (1 mL), HOBt (100 mg, 0.74 mmol), and EDAC (142 mg, 0.74 mmol) were added. The reaction was allowed to stir for 3 h then water (20 mL) was added and the reaction mixture thoroughly shaken to give a precipitate. After filtration and drying under in vacuo the title compound was obtained as a cream solid (69 mg, 44%):

後処理

  1. additionadded to the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customto give a yellow solid which
  4. stirringto stir for 3 h
  5. stirringthe reaction mixture thoroughly shaken
  6. customto give a precipitate
  7. filtrationAfter filtration
  8. dry with materialdrying under in vacuo the title compound

出典と根拠

ORDレコード
ord-a667fa37d5734eeca1814b1d90814af9
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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