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Sodium Hydroxide → 5-(4-Tert-butoxycarbonyl-2-methylpiperazin-1-yl)-4-cyano-2-nitroaniline

HRID 1064366
Notes
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Reaction equation

HRID 1064366 reaction equation
[C:1]([C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:6]([NH2:7])=[CH:5][C:4]=1F)#[N:2].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH:23]([CH3:27])[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].[OH-].[Na+]>CS(C)=O.C(N(C(C)C)CC)(C)C>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:4]2[C:3]([C:1]#[N:2])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:6]([CH:5]=2)[NH2:7])[CH:23]([CH3:27])[CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylateHCID 104197934-Amino-2-fluoro-5-nitrobenzonitrile

Product 1

HCID 222730115-(4-Tert-butoxycarbonyl-2-methylpiperazin-1-yl)-4-cyano-2-nitroanilineYield 76.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl Sulfoxide
Solvent
HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 8.00 g of 4-cyano-3-fluoro-6-nitroaniline (which was synthesized following J. Med. Chem. 1994, 37, 467) and 17.60 g of 1-tert-butoxycarbonyl-3-methylpiperazine in 25 ml of dimethylsulfoxide, 23 ml of diisopropylethylamine was added and stirred for 3 hours at 140° C. and 12 hours at room temperature. 1N aqueous sodium hydroxide solution was added to the reaction liquid which then was extracted with chloroform. The chloroform layer was dried on anhydrous magnesium sulfate and the solvent was distilled off. The residue was washed with chloroform-methanol, to provide 12.2 g of the title compound as a pale yellow solid.

Workup

  1. extractionthen was extracted with chloroform
  2. dry with materialThe chloroform layer was dried on anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. washThe residue was washed with chloroform-methanol

Sources & evidence

ORD record
ord-a5b0314479fb4169b59d127cafa3bada
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06969712B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes