3-Pyridinemethanamine → N5-(3-Pyridylmethyl)-3-(4-fluorophenyl)-1H-5-indazolecarboxamide

HRID 1610101Notes

Reaction equation

HRID 1610101 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][NH2:27])[CH:21]=1>CN(C)C=O.Cl.C(N=C=NCCCN(C)C)C>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][NH:27][C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][N:9]=[C:8]3[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:19])[CH:21]=1

Participants

5

Reactant 2

HCID 310183-PyridinemethanamineHCID 222607223-(4-Fluorophenyl)-1H-Indazole-5-Carboxylic Acid

Product 1

HCID 22260700N5-(3-Pyridylmethyl)-3-(4-fluorophenyl)-1H-5-indazolecarboxamideYield 53.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideSolvent

Procedure

To a solution of 150 mg of 3-(4-fluorophenyl)-1H-5-indazolecarboxylic acid produced in Production Example I-14 in 2.5 ml dimethylformamide were added a solution of 70 mg of 3-picolylamine in 0.5 ml dimethylformamide and 124 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (=WSC.HCl), and the mixture was stirred at room temperature for four days. After removing the solvent by distillation, the residue was dissolved in 25 ml of ethyl acetate. The mixture was sequentially washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The resulting crude crystals were recrystallized from ethyl acetate-diisopropyl ether, to give 109 mg of the title compound as pale yellow crystals.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation
  3. dissolutionthe residue was dissolved in 25 ml of ethyl acetate
  4. washThe mixture was sequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe resulting crude crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-12c9bd26eafb486992feb9bd0881eb27
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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