2,3,6-Trifluorobenzoyl chloride → 6-Chloro-7-(1,1-dimethylethyl)-3-(2,3,6-trifluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 2301339Notes

Reaction equation

[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[C:4](Cl)=O.[Cl:13][C:14]1[N:15]=[N:16][C:17]([NH:24][NH2:25])=[CH:18][C:19]=1[C:20]([CH3:23])([CH3:22])[CH3:21]>CN1CCCC1=O.C(OCC)(=O)C>[Cl:13][C:14]1[C:19]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:18][C:17]2[N:16]([C:4]([C:3]3[C:7]([F:12])=[CH:8][CH:9]=[C:10]([F:11])[C:2]=3[F:1])=[N:25][N:24]=2)[N:15]=1

Participants

Conditions

Temperature: 160 °C

Procedure

2,3,6-Trifluorobenzoyl chloride (4.0 g) was added dropwise to a cooled (15° C.) solution of 3-chloro-4-(1,1-dimethylethyl)-6-hydrazinylpyridazine (4 g) in dry 1-methyl-2-pyrrolidinone (50 ml). After the addition the reaction mixture was heated at 160° C. for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 ml), and washed twice with water (200 ml). The organic phase was separated, dried (sodium sulfate), and evaporated at reduced pressure. The residue was crystallised from dichloromethane on dilution with diethyl ether to afford the title compound (5.3 g) as a colourless solid: 1H NMR (400 MHz, DMSO-d6) δ1.52 (9H, s), 7.50 (1H, m), 7.92 (1H, m), 8.45 (1H, s); MS (ES30) m/z 341/343 [MH]+.

Workup

additionAfter the addition the reaction mixture
temperatureThe reaction mixture was cooled to room temperature
washwashed twice with water (200 ml)
customThe organic phase was separated
dry with materialdried (sodium sulfate)
customevaporated at reduced pressure
customThe residue was crystallised from dichloromethane on dilution with diethyl ether

Sources & evidence

ORD record: ord-d87e228c0c444e09823734aa7bddbb9e
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500828B1

Reaction notes

Loading…