Hydrochloric Acid → 6-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

HRID 40211

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-(6-chloropyridazin-3-yl)hydrazine (1.67 g, 12 mmol), 2-(quinolin-6-yl)acetic acid (1.65 g, 8.8 mmol), and HCl (2000 μl, 24 mmol) was heated in an oil bath at 110° C. for 20 min before it was heated in a microwave (Personal Chemistry) at 180° C.& 15 min. The mixture was quenched with a solution of NaOH (1.2 g, 5 mL) slowly until the suspension is neutral in pH. The mixture was filtered and washed with H2O (2×5 mL). A brown solid was obtained (2.2 g). The solid was treated with aqueous Na2CO3 (3 g, 20 mL, pH ˜11) and heated at 50° C. for 30 min. The blue mixture was cooled to room temperature, and filtered. The black solid was washed with H2O and lyophilized to give the product.

Workup

temperaturewas heated in a microwave (Personal Chemistry) at 180° C.
custom15 min
customThe mixture was quenched with a solution of NaOH (1.2 g, 5 mL) slowly until the suspension
filtrationThe mixture was filtered
washwashed with H2O (2×5 mL)
customA brown solid was obtained (2.2 g)
temperatureheated at 50° C. for 30 min
temperatureThe blue mixture was cooled to room temperature
filtrationfiltered
washThe black solid was washed with H2O
customto give the product

Sources & evidence

ORD record: ord-4a6a7c8a93df4853bd4ec58abf9c7fbf
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524900B2

Linked notes

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