4-Methoxybenzylamine → HCID 58179970, compound

HRID 253963Notes

Reaction equation

HRID 253963 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[N:11][S:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])[C:5](Cl)=[N:6][CH:7]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>O1CCOCC1>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:5]2[C:4]([C:9]3[N:10]=[N:11][S:12][C:13]=3[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=3[Cl:21])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 58180072HCID 58180072, compound

Product 1

HCID 58179970HCID 58179970, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-bromo-2-chloro-3-(5-(2,3-dichlorophenyl)-1,2,3-thiadiazol-4-yl)pyridine (0.37 g, 0.88 mmol) in dioxane (2 mL) was added 4-methoxybenzylamine (4 eq, 460 μL, 3.5 mmol). The solution was heated in a sealed tube at 120° C. for 18 h. After cooling, the mixture was filtered and the filtrate was reduced in vacuo. The resulting oil was purified by silica gel chromatography (5 to 70% EtOAc/hexanes) to provide N-(4-methoxybenzyl)-5-bromo-3-(5-(2,3-dichlorophenyl)-1,2,3-thiadiazol-4-yl)pyridin-2-amine as a yellow sticky solid (415 mg, 90% yield)

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customThe resulting oil was purified by silica gel chromatography (5 to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c0ee3600de99478cb2c57052edf5f851
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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