Methylamine → N-(3-chlorophenyl)-3-((methylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine

HRID 446903Notes

Reaction equation

HRID 446903 reaction equation
Cl[CH2:2][C:3]1[N:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[CH3:20][NH2:21]>O>[Cl:19][C:15]1[CH:14]=[C:13]([NH:12][C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:3]([CH2:2][NH:21][CH3:20])=[N:4][N:5]=3)[N:8]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 593632983-(chloromethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine

Product 1

HCID 59363288N-(3-chlorophenyl)-3-((methylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amineYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Step 3-ii) 3-(Chloromethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine (210 mg, 0.71 mmol) was suspended in 2 mL of 40% methyl amine in water and the suspension microirradiated at 100° C. for 10 min. The reaction mixture was allowed to cool to room temperature and a brown solid was filtered off and dried in vacuo to yield the product, N-(3-chlorophenyl)-3-((methylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine (126 mg, 0.43 mmol, 61% yield): MH+=289.02.

Workup

  1. filtrationa brown solid was filtered off
  2. customdried in vacuo

Sources & evidence

ORD record
ord-f8394ab892c042cf840172a4657b421c
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

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