Hydrochloric Acid → 1-(3-((5,7-Difluoroquinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

HRID 1892446Notes

Reaction equation

Cl.C([O:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([CH2:16][C:17]3[C:18]([F:28])=[C:19]4[C:24](=[CH:25][C:26]=3[F:27])[N:23]=[CH:22][CH:21]=[CH:20]4)=[N:14][N:15]=2)[N:12]=1)=[CH2:6])C>CC(O)=O>[F:28][C:18]1[C:17]([CH2:16][C:13]2[N:11]3[N:12]=[C:7]([C:5](=[O:4])[CH3:6])[CH:8]=[CH:9][C:10]3=[N:15][N:14]=2)=[C:26]([F:27])[CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2

Participants

Conditions

Temperature: 40 °C

Procedure

Aqueous 3N HCl (0.2 mL, 0.6 mmol) was added to a solution of 6-[6-(1-ethoxy-vinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl]-5,7-difluoro-quinoline (87 mg, 0.237 mmol) in HOAc (2 mL). The reaction mixture was stirred at 40° C. for 6 h. LC/MS showed reaction was complete. The solvent was removed in vacuo, and the residue dissolved in EtOAc was neutralized, and extracted with EtOAc. The organic layer was dried, concentrated and purified by flash chromatography to afford 40 mg of the title compound as a pale yellow solid. 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.95 (dd, 1H), 8.56 (d, 1H), 8.29 (d, 1H), 7.85 (d, 1H), 7.60-7.67 (m, 2H), 4.94 (s, 2H), 2.67 (s, 3H). LCMS (method A): [MH]+=339, tR=4.88 min.

Workup

customreaction
customThe solvent was removed in vacuo
dissolutionthe residue dissolved in EtOAc
extractionextracted with EtOAc
customThe organic layer was dried
concentrationconcentrated
custompurified by flash chromatography

Sources & evidence

ORD record: ord-c5e3fc0c2c9943e2b45ff325a7c66c43
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507676B2

Reaction notes

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