Hydrazine → N-(3-aminopropyl)-N-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3-fluoro-4-methylbenzamide

HRID 271828Notes

Reaction equation

HRID 271828 reaction equation
[CH2:1]([C:8]1[C:9]([CH:18]([N:22]([CH2:33][CH2:34][CH2:35][N:36]2C(=O)C3C(=CC=CC=3)C2=O)[C:23](=[O:32])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([F:31])[CH:25]=2)[CH:19]([CH3:21])[CH3:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>C(O)C>[NH2:36][CH2:35][CH2:34][CH2:33][N:22]([CH:18]([C:9]1[C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[CH:19]([CH3:21])[CH3:20])[C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([F:31])[CH:25]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59836196HCID 59836196, compound

Product 1

HCID 11525920N-(3-aminopropyl)-N-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3-fluoro-4-methylbenzamideYield 13.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3-fluoro-N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-4-methylbenzamide 19 (19 mg, 1 eq) in ethanol (1 ml), was added hydrazine (3 μl, 3 eq). The reaction was stirred at room temperature for 2 h then heated to 40° C. for another hour. The precipitate was filtered through a PTFE filter and washed with CH2Cl2. The filtrate was concentrated and purified by flash chromatography to yield 2 mg of N-(3-aminopropyl)-N-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3-fluoro-4-methylbenzamide 2 as a white solid.

Workup

  1. temperaturethen heated to 40° C. for another hour
  2. filtrationThe precipitate was filtered through a PTFE
  3. filtrationfilter
  4. washwashed with CH2Cl2
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-38eac5a30e0c44f7a33f87cdda5192de
Source dataset
uspto-grants-2008_11
Patent number
US07452996B2

Reaction notes

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