Piperazine → HCID 68443918, compound

HRID 388969Notes

Reaction equation

HRID 388969 reaction equation
[NH4+].[OH-].[NH2:3][C:4]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:7]([C:8]([NH:10][C:11]2[CH:19]=[C:18]3[C:14]([CH:15]=[N:16][NH:17]3)=[CH:13][C:12]=2[CH3:20])=[O:9])=[C:6](Cl)[CH:5]=1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>O1CCOCC1>[NH2:3][C:4]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:7]([C:8]([NH:10][C:11]2[CH:19]=[C:18]3[C:14]([CH:15]=[N:16][NH:17]3)=[CH:13][C:12]=2[CH3:20])=[O:9])=[C:6]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:5]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 14923Ammonium HydroxideHCID 68445499HCID 68445499, compound

Product 1

HCID 68443918HCID 68443918, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the amide from above (1 mmol) in dioxane (2 mL) was reacted with aqueous NH4OH using the conditions described in Example 115. After the formation of 4-amino-2-chloro-N-(5-methyl-1H-indazol-6-yl)-5-nitrobenzamide was complete, charged with piperazine (5 mmol). The contents were heated at reflux for 10 h and the reaction mixture was cooled to RT. The contents were poured onto ice cold water with vigorous stirring. The solid formed was collected by filtration, washed with water, and dried in vacuo to provide the product, 4-amino-N-(5-methyl-1H-indazol-6-yl)-5-nitro-2-piperazin-1-yl-benzamide as a yellow solid.

Workup

  1. temperatureThe contents were heated
  2. temperatureat reflux for 10 h
  3. additionThe contents were poured onto ice cold water with vigorous stirring
  4. customThe solid formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-52adc6ac782e4bd184b7ffbe244ddb55
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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