Hydrazine → N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-benzyl}-2-ethyl-butyramide

HRID 1927627Notes

Reaction equation

HRID 1927627 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=CC=[CH:8][CH:9]=2)[C:4](=O)[N:3]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([CH:25]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[O:27])[CH2:21][CH2:20]2)=[C:15]([F:39])[CH:14]=1.NN>C(O)C>[CH2:31]([N:28]([CH2:29][CH3:30])[C:26]([CH:25]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[N:22]1[CH2:21][CH2:20][N:19]([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][NH:3][C:2](=[O:1])[CH:10]([CH2:5][CH3:4])[CH2:9][CH3:8])=[CH:14][C:15]=2[F:39])[CH2:24][CH2:23]1)=[O:27])[CH3:32]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 69304319HCID 69304319, compound

Product 1

HCID 58870687N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-benzyl}-2-ethyl-butyramideYield 50.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-{4-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-fluoro-phenyl]-piperazin-1-yl}-N,N-diethyl-2-phenyl-acetamide (0.09 g, 0.16 mmol) in ethanol (3 mL) was added hydrazine (50 μL) and the mixture stirred at rt. After 6 h, the solvent was removed and the residue treated with 2-ethyl-butyryl chloride (30 μL) as described in previous examples to provide 0.04 g of the title compound. MS: 497.6. 1H NMR (CDCl3): 7.47-7.43 (m, 2H), 7.37-7.29 (m, 3H), 6.96-6.91 (m, 2H), 6.88-6.84 (m, 1H), 5.72-5.67 (br, 1H), 4.37 (d, J=5.3, 2H), 4.23 (s, 1H), 3.49-3.36 (m, 2H), 3.31-3.15 (m, 2H), 3.14-3.05 (m, 4H), 2.74-2.63 (m, 4H), 1.89-1.82 (m, 1H), 1.68-1.58 (m, 2H), 1.53-1.43 (m, 2H), 1.10-1.01 (m, 6H), 0.91-0.86 (m, 6H).

Workup

  1. customthe solvent was removed
  2. additionthe residue treated with 2-ethyl-butyryl chloride (30 μL)

Sources & evidence

ORD record
ord-ce673af2bc3f4be09a8e29ccd7c1e6a7
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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