Ammonium Hydroxide → HCID 68444152, compound

HRID 388954Notes

Reaction equation

HRID 388954 reaction equation
Cl[C:2]1[CH:19]=[C:18](F)[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[N:12][NH:13]2)=[CH:9][CH:8]=1)=[O:5].[NH4+].[OH-].[NH2:26]C1C=C(F)C([N+]([O-])=O)=CC=1C(NC1C=C2C(C=NN2)=CC=1)=O.[CH3:49][CH:50]1[CH2:55][NH:54][CH2:53][CH:52]([CH3:56])[NH:51]1>O1CCOCC1>[NH2:26][C:18]1[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:3]([C:4]([NH:6][C:7]2[CH:15]=[C:14]3[C:10]([CH:11]=[N:12][NH:13]3)=[CH:9][CH:8]=2)=[O:5])=[C:2]([N:54]2[CH2:53][CH:52]([CH3:56])[NH:51][CH:50]([CH3:49])[CH2:55]2)[CH:19]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 660562,6-DimethylpiperazineHCID 68443954HCID 68443954, compoundHCID 68446177HCID 68446177, compound

Product 1

HCID 68444152HCID 68444152, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-chloro-4-fluoro-N-(1H-indazol-6-yl)-5-nitrobenzamide (1 mmol) in dioxane (2 mL) was reacted with aqueous NH4OH using the conditions described in Example 115. After the formation of 2-amino-4-fluoro-N-(1H-indazol-6-yl)-5-nitrobenzamide was complete, the reaction mixture was charged with 2,6-dimethylpiperazine (6 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-2-(3,5-dimethyl-piperazin-1-yl)-N-(1H-indazol-6-yl)-5-nitrobenzamide 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-f3002b9760fe4eeea15f6c5c3d51cbbd
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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