6-Chloro-3-hydrazinylpyridazin-4-amine → 6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine

HRID 873974Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11]([O-])(=O)[CH3:12].[K+]>CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]2[N:6]([C:11]([CH3:12])=[N:9][N:8]=2)[N:7]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A MW vial was charged with 6-chloro-3-hydrazinylpyridazin-4-amine (Step 112.2) (475 mg, 2.98 mmol) and potassium acetate (467 mg, 4.76 mmol) in AcOH (5 mL). The MW vial was sealed and the resulting mixture was heated up and stirred at 170° C. for 4 hr. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 1-3%) to afford the title product (450 mg, 2.451 mmol, 82% yield). tR: 2.32 min (HPLC 1); tR: 0.55 min (LC-MS 2); ESI-MS: 184 [M+H]+ (LC-MS 2); ESI-MS: 182 [M−H]− (LC-MS 2); Rf=0.45 (CH2Cl2/MeOH 9:1).

Workup

customThe MW vial was sealed
temperaturethe resulting mixture was heated up
temperatureThe reaction was cooled down to RT
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 1-3%)

Sources & evidence

ORD record: ord-768931d1870a45dea662c9381940b6b9
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975417B2

Reaction notes

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