2,4-Dimethoxybenzylamine → HCID 58180520, compound

HRID 1188020Notes

Reaction equation

HRID 1188020 reaction equation
Cl[C:2]1[C:7]2[N:8]=[CH:9][N:10]([CH3:11])[C:6]=2[CH:5]=[C:4]([Cl:12])[N:3]=1.[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18]>O>[Cl:12][C:4]1[N:3]=[C:2]([NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=2[O:14][CH3:13])[C:7]2[N:8]=[CH:9][N:10]([CH3:11])[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 577543464,6-Dichloro-1-methyl-1H-imidazo[4,5-c]pyridine

Product 1

HCID 58180520HCID 58180520, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

In a 200 mL round bottom flask, 4,6-dichloro-1-methyl-1H-imidazo[4,5-c]pyridine (15 g, 74.2 mmol) (prepared as per WO2006122137 example A1.5) was dissolved in 2,4-dimethoxybenzylamine (25 mL, 166 mmol). The reaction mixture was heated to 110° C. for 3 h and cooled to room temperature. Water was added and a tan colored solid precipitated out. Vacuum filtration yielded a tan solid. The solid was washed with ethyl acetate and hexane to yield 6-chloro-N-(2,4-dimethoxybenzyl)-1-methyl-1H-imidazo[4,5-c]pyridin-4-amine (23.459 g, 95% yield) as a cream colored solid.

Workup

  1. temperaturecooled to room temperature
  2. customa tan colored solid precipitated out
  3. filtrationVacuum filtration
  4. customyielded a tan solid
  5. washThe solid was washed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-d36879a2422341189e08842b239ddb63
Source dataset
uspto-grants-2014_03
Patent number
US08673933B2

Reaction notes

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