Triethylamine → [4,5-Dimethyl-6-((R)-3-methyl-piperazin-1-yl)-pyridazin-3-yl]-pyridin-3-yl-methanone

HRID 1479962Notes

Reaction equation

HRID 1479962 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[C:4]([CH3:16])[C:3]=1[CH3:17].[CH3:18][C@H:19]1[NH:24][CH2:23][CH2:22][NH:21][CH2:20]1.C(N(CC)CC)C>CN1C(=O)CCC1>[CH3:16][C:4]1[C:3]([CH3:17])=[C:2]([N:21]2[CH2:22][CH2:23][NH:24][C@H:19]([CH3:18])[CH2:20]2)[N:7]=[N:6][C:5]=1[C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73304342-Methylpiperazine, (R)-HCID 59191601HCID 59191601, compound

Product 1

HCID 59191636[4,5-Dimethyl-6-((R)-3-methyl-piperazin-1-yl)-pyridazin-3-yl]-pyridin-3-yl-methanoneYield 90%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(6-Chloro-4,5-dimethyl-pyridazin-3-yl)-pyridin-3-yl-methanone (1.2 g, 4.84 mmol) and (R)-2-methy 1-piperazine (485 mg, 4.84 mmol) are added to a microwave vial followed by NMP (17 mL) and triethylamine (2.01 mL, 14.49 mmol). The vial is sealed and irradiated in the microwave at 170° C. for 30 min. The crude material is directly purified via flash chromatography on silica gel (0-20% methanol in CH2Cl2). The resulting oil is co-evaporated with CH2Cl2 and heptane to afford the title compound as a powder (1350 mg, 90%).

Workup

  1. customThe vial is sealed
  2. customirradiated in the microwave at 170° C. for 30 min
  3. customThe crude material is directly purified via flash chromatography on silica gel (0-20% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-e88e0ce41efa4312b6612cfc3cbccfbb
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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