Sodium Hydroxide → 4-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid

HRID 1755336Notes

Reaction equation

HRID 1755336 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:28]=[CH:29][N:30]=3)[N:15]=[C:16]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=3)[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>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:28]=[CH:29][N:30]=3)[N:15]=[C:16]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=3)[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86682718Methyl 4-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate

Product 1

HCID 715258044-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acidYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 4-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (0.135 g, 0.333 mmol) in dioxane (20 mL) and H2O (10 mL) was added NaOH (133 mg, 3.33 mmol) at 25° C. After 2 h the mixture was washed with ether (10 mL) and the aqueous layer was adjusted to pH=4 with concentrated HCl, then it was concentrated and filtered. The solid was washed with ether and dried to afford 4-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (0.101 g, 77%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 9.98 (s, 1H), 8.57 (s, 1H), 8.24 (s, 1H), 8.11-8.03 (m, 4 h), 7.69 (s, 1H), 7.43 (d, 1H, J=8.4 Hz), 7.13 (d, 1H, J=8.7 Hz), 4.04 (s, 3H), 3.79 (s, 3H). LC-MS: [M+H]+, 391.9, tR=1.454 min, HPLC: 98.08% at 214 nm, 95.71% at 254 nm, tR=3.628 min.

Workup

  1. washAfter 2 h the mixture was washed with ether (10 mL)
  2. concentrationit was concentrated
  3. filtrationfiltered
  4. washThe solid was washed with ether
  5. customdried

Sources & evidence

ORD record
ord-f58431d0ab6348c2b808b28d8afc0d96
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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