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Ammonium Hydroxide → HCID 68445414, compound

HRID 1163429
Notes
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Reaction equation

HRID 1163429 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][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]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:53]2[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]2)[CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 531671-MethylpiperazineHCID 68443954HCID 68443954, compoundHCID 68446177HCID 68446177, compound

Product 1

HCID 68445414HCID 68445414, compound

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

A solution of 2-chloro-4-fluoro-N-(1H-indazol-6-yl)-5-nitrobenzamide (10 mmol) in dioxane (20 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 N-methylpiperazine (40 mmol) (NMP). 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-(1H-indazol-6-yl)-2-(4-methylpiperazin-1-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-daef5e2a92ba4d31ae698ca703548882
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07820821B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes