2-(Benzylamino)-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine → HCID 10220931, compound

HRID 1635489Notes

Reaction equation

HRID 1635489 reaction equation
C([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=3)[N:18]=[C:17]([CH3:27])[CH:16]=2)[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[NH2:8][C:9]1[CH:14]=[C:13]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=3)[N:18]=[C:17]([CH3:27])[CH:16]=2)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 1

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

Product 1

HCID 10220931HCID 10220931, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-benzylamino-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 19; 1.03 g, 0.0029 mol) and palladium hydroxide (0.2 g)in acetic acid was hydrogenated under 60 psi at 40° C. for 9 hours. The mixture was cooled and filtered through a pad of Celite™. The filtrate was concentrated and purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 0.43 g of product as a white solid: mp: 124-125° C.; Anal. Calc'd. for C16H16N4: C, 72.70; H, 6.10; N, 21.20. Found: C, 72.41; H, 6.31; N, 20.63.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through a pad of Celite™
  3. concentrationThe filtrate was concentrated
  4. custompurified by chromatography on silica gel (ethyl acetate/hexane, 1:1)

Sources & evidence

ORD record
ord-cf0dfa9058df436b92e08c01328c8ddc
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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