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

HRID 1064366Notes

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]

Participants

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

extractionthen was extracted with chloroform
dry with materialThe chloroform layer was dried on anhydrous magnesium sulfate
distillationthe solvent was distilled off
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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