Hydrochloric Acid → 3-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid

HRID 1755432Notes

Reaction equation

HRID 1755432 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]2[C:13]3[N:14]([CH:29]=[CH:30][N:31]=3)[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=3)[C:21]([O:23]CC)=[O:22])[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10].[Li+].[OH-].Cl>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]2[C:13]3[N:14]([CH:29]=[CH:30][N:31]=3)[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=3)[C:21]([OH:23])=[O:22])[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71534335HCID 71534335, compound

Product 1

HCID 715343363-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (150 mg, 358 μmol) was dissolved in dioxane (18 mL). To this was added a solution of LiOH (85.6 mg, 3.58 mmol) in water (9 mL). The mixture was stirred for 4 h, acidified with 1N HCl, and concentrated in vacuo to give the crude acid which was recrystallized from isopropyl alcohol and methanol to give 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (123 mg, 314 μmol, 88%) as a light brown powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.97 (s, 1H) 8.60 (s, 1H) 8.52 (s, 1H) 8.17-8.30 (m, 2H) 8.05 (d, J=7.55 Hz, 1H) 7.60-7.72 (m, 2H) 7.41 (d, J=8.31 Hz, 1H) 7.12 (d, J=8.31 Hz, 1H) 4.05 (s, 3H) 3.76 (s, 3H); LC/MS: 391.8 [MH]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give the crude acid which
  3. customwas recrystallized from isopropyl alcohol and methanol

Sources & evidence

ORD record
ord-04ad343a232745dbb1f24d5b25a8fcc5
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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