Hydrochloric Acid → 6-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)isoquinoline hydrochloride

HRID 219190Notes

Reaction equation

HRID 219190 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7](B3OC(C)(C)C(C)(C)O3)[CH:8]=2)[C:3]1=O.CN1C[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:31]3[CH:32]=[CH:33][C:34]4[N:35]([C:37]([CH2:40]NC(=O)OC(C)(C)C)=[N:38][N:39]=4)[N:36]=3)[CH:28]=2)C1=O.[ClH:50]>>[ClH:50].[C:27]1([C:31]2[CH:32]=[CH:33][C:34]3[N:35]([C:37]([CH2:40][C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[CH:10]=[N:2][CH:1]=[CH:3]5)=[N:38][N:39]=3)[N:36]=2)[CH:26]=[CH:25][CH:24]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 57691219Tert-butyl (6-(2-methyl-1-oxoisoindolin-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamateHCID 576912242-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one

Product 1

HCID 675031546-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)isoquinoline hydrochloride

Procedure

A 10 mL, CEM microwave vessel was charged with 3 (0.1040 g, 0.427 mmol), 1-(5-phenylpyridin-2-yl)hydrazine (4, 0.119 g, 0.641 mmol), a stirbar and 1 mL concentrated HCl. The vessel was sealed, and fitted with an 18-guage needle and an Argon inlet. The slurry was placed in a heating block at 115° C. for 15 minutes with stirring. A volatile substance evolved during this time. The vessel was briefly cooled, and the seal was replaced. The vessel was irradiated on a CEM Explorer using the following parameters: ramp time 20 s, hold time 10 min, hold temperature 150° C., powermax=on, 75 W max. The resultant turbid aqueous solution was filtered and concentrated in vacuo. The solids were suspended in 3 mL hot EtOH, and cooled. The precipitate was isolated by filtration and washed with EtOH (3×3 mL). The solids were taken up in 2 mL H2O, and filtered through a 0.1 μm PVDF Ultra-free-CL centrifugal filter (Millipore Corp, PN UFC40W00, 2000 g for 5 minutes). The aqueous filtrate was lyophilized to afford 6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)isoquinoline hydrochloride. Anal. Calcd for C21H15N5. HCl.1.7H2O: C, 62.36; H, 4.83; N, 17.31. Found: C, 62.39±0.08; H, 4.48±0.02; N, 17.28±0.03.

Workup

  1. customThe vessel was sealed
  2. customfitted with an 18-guage needle and an Argon inlet
  3. temperatureThe vessel was briefly cooled
  4. customThe vessel was irradiated on a CEM Explorer
  5. customtime 20 s
  6. customtime 10 min
  7. customtemperature 150° C., powermax=
  8. filtrationwas filtered
  9. concentrationconcentrated in vacuo
  10. temperaturecooled
  11. customThe precipitate was isolated by filtration
  12. washwashed with EtOH (3×3 mL)
  13. filtrationfiltered through a 0.1 μm PVDF Ultra-free-CL centrifugal
  14. filtrationfilter (Millipore Corp, PN UFC40W00, 2000 g for 5 minutes)

Sources & evidence

ORD record
ord-e66bd2e8c4344c19af9073d4d6c28bfa
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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