HCID 58026183, compound → HCID 24826050, compound

HRID 1514362Notes

Reaction equation

HRID 1514362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][N:12]=[C:11]([N:18]3[CH:26]=[C:25]4[C:20]([CH:21]=[CH:22][CH:23]=[CH:24]4)=[N:19]3)[N:10]=2)=[CH:4][CH:3]=1>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][N:12]=[C:11]([N:18]3[CH:26]=[C:25]4[C:20]([CH:21]=[CH:22][CH:23]=[CH:24]4)=[N:19]3)[N:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58026183HCID 58026183, compound

Product 1

HCID 24826050HCID 24826050, compoundYield 4.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(4-Chloro-phenyl)-(2-indazol-2-yl-5-nitro-pyrimidin-4-yl)-amine (600 mg, 1.64 mmol) was dissolved in methanol (30 mL), palladium an carbon (10%, 150 mg) was added and the reaction mixture was stirred under a hydrogen atmosphere at room temperature over night. Filtration and evaporation gave the crude product which was purified by preparative HPLC to give N-(4-chloro-phenyl)-2-indazol-2-yl-pyrimidine-4,5-diamine (27 mg, 4.9%) as a brown solid. LC-ESI-HRMS of [M+H]+ shows 337.0955 Da. Calc. 337.096847 Da, dev. −4 ppm.

Workup

  1. filtrationFiltration and evaporation
  2. customgave the crude product which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-e8158035a3084fb79dcfeb2718f3f1a4
Source dataset
uspto-grants-2012_07
Patent number
US08222262B2

Reaction notes

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