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

HRID 1713729노트

반응식

HRID 1713729 반응식
[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

참가 물질

8

반응물 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-carboxylate2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매3회HCID 6228Dimethylformamide용매2회

실험 절차

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%):

후처리

  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

출처 및 근거

ORD 기록
ord-a667fa37d5734eeca1814b1d90814af9
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

반응 노트

불러오는 중…