Sodium Hydroxide → HCID 71525361, compound

HRID 1755352Notes

Reaction equation

HRID 1755352 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH:7]([CH3:9])[CH2:6][N:5]([C:10]2[N:15]=[C:14]([NH:16][C:17]3[C:18]4[N:19]([CH:33]=[CH:34][N:35]=4)[N:20]=[C:21]([C:23]4[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=4)[C:26]([O:28]C)=[O:27])[CH:22]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:4]1.[OH-].[Na+]>O1CCOCC1.O>[CH3:2][CH:3]1[CH2:8][CH:7]([CH3:9])[CH2:6][N:5]([C:10]2[N:15]=[C:14]([NH:16][C:17]3[C:18]4[N:19]([CH:33]=[CH:34][N:35]=4)[N:20]=[C:21]([C:23]4[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=4)[C:26]([OH:28])=[O:27])[CH:22]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86682722HCID 86682722, compound

Product 1

HCID 71525361HCID 71525361, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 3-(8-(6-(3,5-dimethylpiperidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate hydrochloride (0.025 g, 0.055 mmol) in dioxane (10 mL) and H2O (5 mL) was added NaOH (22 mg, 0.55 mmol) at 40° C. After 2 h the mixture was washed with ether (10 mL) and the aqueous layer was adjusted to pH=4, then filtered. The solid was washed with ether and dried to afford 3-(8-(6-(3,5-dimethylpiperidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (0.017 g, 70%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 9.99 (s, 1H), 8.67 (s, 1H), 8.52 (s, 1H), 8.35 (s, 1H), 8.19 (d, 1H, J=7.8 Hz), 8.09 (d, 1H, J=7.8 Hz), 7.84 (s, 1H), 7.71-7.49 (m, 2H), 6.76-6.72 (m, 1H), 6.52-6.48 (m, 1H), 4.22 (d, 1H, J=12.6 Hz), 3.65-3.59 (m, 1H), 3.28-3.21 (m, 1H), 2.33 (t, 1H, J=12.0 Hz), 1.92-1.41 (m, 4 h), 0.80-0.69 (m, 6H). LC-MS: [M+H]+, 443, tR=1.825 min, HPLC: 98.43% at 214 nm, 99.05% at 254 nm, tR=6.85 min.

Workup

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

Sources & evidence

ORD record
ord-51e74d9f14ed4c3aa81c38fc29658881
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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