Triethylamine → (R)-4-(6-Chloro-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H [1,2']bipyrazinyl-5'-carboxylic acid methyl ester

HRID 447112Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:10]2[CH2:15][CH2:14][NH:13][C@H:12]([CH3:16])[CH2:11]2)=[C:6]([CH3:9])[C:7]=1[CH3:8].[CH3:17][O:18][C:19]([C:21]1[CH:26]=[N:25][C:24](Cl)=[CH:23][N:22]=1)=[O:20].C(N(CC)CC)C>O1CCOCC1>[CH3:17][O:18][C:19]([C:21]1[N:22]=[CH:23][C:24]([N:13]2[CH2:14][CH2:15][N:10]([C:5]3[N:4]=[N:3][C:2]([Cl:1])=[C:7]([CH3:8])[C:6]=3[CH3:9])[CH2:11][C@H:12]2[CH3:16])=[N:25][CH:26]=1)=[O:20]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Chloro-4,5-dimethyl-6-((R)-3-methyl-piperazin-1-yl)-pyridazine (1.20 g, 4.88 mmol), 5-chloro-pyrazine-2-carboxylic acid methyl ester (946 mg, 5.37 mmol), triethylamine (3.40 mL, 24.4 mmol), and 1,4-dioxane (10 mL) are combined in a 100 mL round-bottom flask fitted with a reflux condenser and heated to 80° C. for 24 h. The reaction is then allowed to cool to room temperature and stirred for 48 h. A beige solid precipitates during this time which is isolated by filtration, rinsing with H2O. The precipitate is dried in vacuo to afford the title compound (1.30 g, 71%).

Workup

customfitted with a reflux condenser
temperatureto cool to room temperature
customA beige solid precipitates during this time which
customis isolated by filtration
washrinsing with H2O
customThe precipitate is dried in vacuo

Sources & evidence

ORD record: ord-1f747d21999d49bf83725ce9c7d20541
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481542B2

Reaction notes

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