Hydrochloric Acid → HCID 57929863, compound

HRID 1930057Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][N:12]=[C:11]([NH2:14])[C:10]=1[C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([CH:24]([CH3:26])[CH3:25])=[N:22][N:23]=2)[N:20]=1.Cl.CO[CH:30](OC)[CH2:31][CH:32](OC)OC.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].CCO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([CH:24]([CH3:26])[CH3:25])=[N:22][N:23]=3)[N:20]=2)=[C:11]2[N:14]=[CH:30][CH:31]=[CH:32][N:12]2[N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The 5-(2,4-difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-3-amine (0.200 g, 0.563 mmol, Example #23) and zinc chloride (0.038 g, 0.281 mmol) were added to EtOH (1 mL). Concentrated HCl (1.0 mL, 33 mmol) was added followed by malonaldehyde bis(dimethyl acetal) (0.111 g, 0.675 mmol). The mixture was heated to about 80° C. for about 15 min then the mixture was poured onto ice and basified with 50% aqueous NaOH. The mixture was extracted with EtOAc then the organic solution was dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel with DCM/MeOH (9:1) as an eluent to give the title compound (0.133 g, 60%): LC/MS (Table 1, Method a) Rt=3.05 min; MS m/z: 392.3 (M+H)+.

Workup

additionthe mixture was poured onto ice
extractionThe mixture was extracted with EtOAc
dry with materialthe organic solution was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe material was purified by flash chromatography on silica gel with DCM/MeOH (9:1) as an eluent

Sources & evidence

ORD record: ord-b9ef8f9c687048a5a2f867fa6fdc263b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188083B2

Reaction notes

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