Benzylamine → 2-(Benzylamino)-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

HRID 1635487Notes

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

Participants

Reactant 2

HCID 7504Benzylamine2×

HCID 114829832-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

Product 1

HCID 98415332-(Benzylamino)-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridineYield 85%

Procedure

A mixture of 2-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 45; 1.24 g, 0.0044 mol) and benzylamine (40 mL) was heated at 180° C. for 20 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 product was purified by chromatography on silica gel (ethyl acetate/hexane, 3:7) to give 1.33 g (85% yield) of the titled compound as a clear oil, which solidified upon standing: mp: 73-75° C. Anal. Calc'd. for C23H22N40.2H2O: C, 76.83; H, 6.39; N, 15.06. Found: C, 76.88; H, 6.37; N, 14.92.

Workup

customwas removed under vacuum
customthe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated
customthe crude product was purified by chromatography on silica gel (ethyl acetate/hexane, 3:7)

Sources & evidence

ORD record: ord-944c39dc0a564d278a72e8d3c7c516db
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509361B1

Reaction notes

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