Methanol → HCID 58190488, compound
Reaction equation
[OH2:1].NN.[OH:4][CH2:5][CH2:6][O:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].[CH3:19]O>>[OH:4][CH2:5][CH:6]([O:7][N:8]1[C:9](=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]1=[O:17])[CH2:19][OH:1]Participants
Procedure
Hydrazine monohydrate (3.96 mg, 0.124 mmol) was added to a solution of 2-(2-hydroxyethoxy)isoindoline-1,3-dione (produced with a similar procedure for intermediate B) (25.6 mg, 0.124 mmol) in 5 mL of MeOH. The solution was heated at reflux for 2 h and then cooled to rt. White precipitate was filtered off and 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (41.2) (15 mg, 0.049 mmol) was added. The pH value of the solution was adjusted to 5-6 with 1N HCl solution. The reaction solution was then stirred at it for 2 h. Solvent was evaporated and the crude was purified by HPLC (acidic with 0.05% TFA) to give 8 mg (44.5%) of the title compound as a white TFA salt. 1H-NMR (400 MHz, MeOH-d4) δ ppm 9.09 (s, 1H), 8.93 (d, 1H), 8.27 (s, 1H), 8.16 (m, 3H), 7.98 (d, 1H), 7.93 (m, 1H), 4.92 (s, 2H), 4.38 (t, 2H), 3.86 (t, 2H), 2.34 (s, 3H). LC-MS (method B): [MH]+=363.1, tR=2.31 min.
Sources & evidence
- ORD record
- ord-a23b05c399824e78ac15e80e3c7b5d2d
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507676B2
Reaction notes
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