Methylamine → 2-(4-methoxybenzyl)-5-bromo-4-(methylamino)pyridazin-3(2H)-one

HRID 1253625Notes

Reaction equation

HRID 1253625 reaction equation
[CH3:1][NH2:2].[CH3:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][N:10]2[C:15](=[O:16])[C:14](Br)=[C:13]([Br:18])[CH:12]=[N:11]2)=[CH:7][CH:6]=1>C1(C)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][N:10]2[C:15](=[O:16])[C:14]([NH:2][CH3:1])=[C:13]([Br:18])[CH:12]=[N:11]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 469304402-(4-methoxybenzyl)-4,5-dibromopyridazin-3(2H)-one

Product 1

HCID 469304412-(4-methoxybenzyl)-5-bromo-4-(methylamino)pyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

In a glass pressure reactor vessel equipped with a magnetic stir bar, toluene (100 mL) was saturated with anhydrous methylamine at 0° C. then 2-(4-methoxybenzyl)-4,5-dibromopyridazin-3(2H)-one (1) (22 g, 59 mmol) was added. The vessel was sealed and the suspension was stirred and heated at 90° C. for 18 h. The resulting suspension was allowed to cool to RT. Anhydrous methylamine was bubbled through the mixture for 15 min, the reactor was sealed again, and the mixture was stirred and heated at 90° C. for an additional 18 h. After cooling to RT, the mixture was concentrated in vacuo to dryness. The resulting brown solid was suspended in MeOH and sonicated. The solid was collected by suction filtration, washed with MeOH, and dried in vacuo to give 2-(4-methoxybenzyl)-5-bromo-4-(methylamino)pyridazin-3(2H)-one as a yellow solid.

Workup

  1. customIn a glass pressure reactor vessel equipped with a magnetic stir bar
  2. customThe vessel was sealed
  3. temperatureto cool to RT
  4. customAnhydrous methylamine was bubbled through the mixture for 15 min
  5. customthe reactor was sealed again
  6. stirringthe mixture was stirred
  7. temperatureheated at 90° C. for an additional 18 h
  8. temperatureAfter cooling to RT
  9. concentrationthe mixture was concentrated in vacuo to dryness
  10. customsonicated
  11. filtrationThe solid was collected by suction filtration
  12. washwashed with MeOH
  13. customdried in vacuo

Sources & evidence

ORD record
ord-769048511e8e42adbc7bb63f129fd0de
Source dataset
uspto-grants-2013_06
Patent number
US08455495B2

Reaction notes

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