3-Aminopyridine → HCID 86679704, compound

HRID 2367709Notes

Reaction equation

HRID 2367709 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[C:18](O)=[O:19].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[C:18]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:19]

Participants

6

Reactant 4

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 71573585-bromo-1H-indazole-3-carboxylic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86679704HCID 86679704, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 3-aminopyridine (CXXV) (0.195 g, 0.2.07 mmol) in DMF (10 mL) was added 5-bromo-1H-indazole-3-carboxylic acid (CXV) (0.500 g, 0.2.07 mmol) and N,N-diisopropylethylamine (0.723 mL, 4.15 mmol). The reaction mixture was cooled to 0° C. and added with HATU (0.787 g, 2.07 mmol). The reaction mixture was allowed to warm to room temperature and stirred for an additional 2 h. The solution was concentrated under vacuum. The residue was purified by column chromatography (1:99 MeOH[7N NH3]:CHCl3→4:96 MeOH[7N NH3]:CHCl3) to afford 5-bromo-N-(pyridin-3-yl)-1H-indazole-3-carboxamide (CXXXV) (0.200 g, 0.63 mmol, 30% yield) as a white solid. ESIMS found for C13H9BrN4O m/z 318.0 (M+H).

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe solution was concentrated under vacuum
  3. customThe residue was purified by column chromatography (1:99 MeOH[7N NH3]:CHCl3→4:96 MeOH[7N NH3]:CHCl3)

Sources & evidence

ORD record
ord-bb3027941eeb4ec8adefc45b2a088536
Source dataset
uspto-grants-2014_04
Patent number
US08697887B2

Reaction notes

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