Water → 6-(1-(2,6-Dichlorophenyl)-3-(2,4-difluorophenyl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1929987Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17]([CH:20]([CH3:22])[CH3:21])=[N:18][N:19]=2)[N:16]=1.Cl.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[NH:33][NH2:34].[CH3:35]OC(OC)N(C)C.O>CCO>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[N:33]1[CH:35]=[C:10]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:17]([CH:20]([CH3:22])[CH3:21])=[N:18][N:19]=3)[N:16]=2)[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[N:34]1

Participants

Conditions

Temperature: 85 °C

Procedure

The 1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.200 g, 0.632 mmol, Preparation #K.1) in EtOH (2 mL) was treated with (2,6-dichlorophenyl)hydrazine hydrochloride (0.148 g, 0.696 mmol) then the mixture was heated at about 85° C. for about 10 min. The mixture was cooled then N,N-dimethylformamide dimethyl acetal (1.50 mL, 11.2 mmol) was added and the mixture was heated to about 85° C. for about 1 h. The mixture was cooled then water (2 mL) was added and the mixture was heated to about 60° C. for about 20 min. The mixture was then allowed to cool to ambient temperature then purified by RP-HPLC (Table 1, Method f) to give the title compound (0.107 g, 35%): LC/MS (Table 1, Method g) Rt=2.93 min; MS m/z: 485.2 (M+H)+.

Workup

temperatureThe mixture was cooled
temperaturethe mixture was heated to about 85° C. for about 1 h
temperatureThe mixture was cooled
temperaturethe mixture was heated to about 60° C. for about 20 min
temperatureto cool to ambient temperature
customthen purified by RP-HPLC (Table 1, Method f)

Sources & evidence

ORD record: ord-b5c4baf9c82a49339fb926a7bd54611a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188083B2

Reaction notes

Loading…