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

HRID 1713729Notes

Reaction equation

HRID 1713729 reaction equation
[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

Participants

8

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent2×

Procedure

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%):

Workup

  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

Sources & evidence

ORD record
ord-a667fa37d5734eeca1814b1d90814af9
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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