6-Amino-3-chloropyridazine → 6-([1,2,4]Triazolo[4,3-a]pyridin-3-ylthio)pyridazin-3-amine

HRID 1925103Notes

Reaction equation

[N:1]1[N:2]=[C:3]([SH:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl[C:12]1[N:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=1>C(O)(=O)C>[N:1]1[N:2]=[C:3]([S:10][C:12]2[N:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A reaction mixture of [1,2,4]triazolo[4,3-a]pyridine-3-thiol (8.49 g, 55.0 mmol) and 6-chloropyridazin-3-amine (6.82 g, 50 mmol) in acetic acid (100 mL) was heated at 80° C. for 20 hrs. The reaction was stripped to dryness via rotary evaporation and the resulting material was suspended in H2O (100 mL). To this suspension, solid Na2CO3 was added in portions until pH 10 was achieved and then the mixture was sonicated. The resulting solid was collected by filtration and rinsed thoroughly with water followed by ethyl ether. The solid was dried in vacuum over P2O5 to provide the title compound, 6-([1,2,4]Triazolo[4,3-a]pyridin-3-ylsulfanyl)-pyridazin-3-ylamine, as a white power (11.0 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.15-7.25 (m, 1 H) 7.53-7.58 (m, 1 H) 7.61 (ddd, J=9.22, 6.69, 1.26 Hz, 1 H) 7.84-7.90 (m, 1 H) 7.99 (dt, J=9.09, 1.01 Hz, 1 H) 8.51 (dt, J=7.01, 1.04 Hz, 1 H) 8.79 (br. s., 2 H). ESI-MS:m/z 553.2 (M+H)+.

Workup

customThe reaction was stripped to dryness via rotary evaporation
additionTo this suspension, solid Na2CO3 was added in portions until pH 10
customthe mixture was sonicated
filtrationThe resulting solid was collected by filtration
washrinsed thoroughly with water
dry with materialThe solid was dried in vacuum over P2O5

Sources & evidence

ORD record: ord-b8b7b81b2dd34aa9a324e77298c186f5
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178534B2

Reaction notes

Loading…