3-Pyridinemethanamine → HCID 9841763, compound

HRID 1635507Notes

Reaction equation

HRID 1635507 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[N:11]=[C:10]([CH3:20])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1>O>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][NH:21][C:2]2[CH:7]=[C:6]([C:8]3[N:12]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=4)[N:11]=[C:10]([CH3:20])[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 18676089HCID 18676089, compound

Product 1

HCID 9841763HCID 9841763, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 2-chloro-4-[1-(3-fluorophenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 47; 0.48 g, 0.0017 mol) and 3-(aminomethyl)pyridine (10 mL) was heated at 190° C. overnight (about eighteen hours). The reaction mixture was cooled, treated with copious amount of water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/triethylamine, 99:1) to give 0.35 g (60% yield) of product as a yellow oil: Anal. Calc'd. for C21H18FN5: C, 70.18; H, 5.05; N, 19.49. Found: C, 69.78; H, 5.35; N, 18.87.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe crude was purified by chromatography on silica gel (ethyl acetate/triethylamine, 99:1)

Sources & evidence

ORD record
ord-603d74db68d3411c939587f787a73881
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

Loading…