Benzylamine → HCID 9798212, compound

HRID 1635497Notes

Reaction equation

HRID 1635497 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([NH:27][C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 18676092HCID 18676092, compound

Product 1

HCID 9798212HCID 9798212, compoundYield 89%

Conditions

Temperature
180 °C

Procedure

A mixture of 2-chloro-4-[1-(4-fluorophenyl)-1H-pyrazol-5-yl]pyridine (Example 46; 0.56 g, 0.002 mol) and benzylamine (20 mL) was heated at 180° C. overnight (about eighteen hours). The excess benzylamine was removed under vacuum and the residue was partitioned between ethyl acetate and water. 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/hexane, 3:7) to give 0.63 g (89% yield) of product as a white solid: mp: 125-127° C.; Anal. Calc'd. for C22H17FN4: C, 73.24; H, 4.98; N, 16.27. Found: C, 72.89; H, 4.69; N, 15.82.

Workup

  1. customThe excess benzylamine was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  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/hexane, 3:7)

Sources & evidence

ORD record
ord-8219c1e570484ca5bc074cb9ab47f468
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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