Sodium Hydroxide → HCID 86682734, compound

HRID 1755380Notes

Reaction equation

HRID 1755380 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[C:16]4[N:17]([CH:31]=[CH:32][N:33]=4)[N:18]=[C:19]([C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([O:26]C)=[O:25])[CH:20]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH-].[Na+]>O1CCOCC1.O>[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[C:16]4[N:17]([CH:31]=[CH:32][N:33]=4)[N:18]=[C:19]([C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([OH:26])=[O:25])[CH:20]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86682733HCID 86682733, compound

Product 1

HCID 86682734HCID 86682734, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 3-(8-(6-(4,4-dimethylpiperidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (200 mg, 0.44 mmol) and NaOH (200 mg, 5 mmol) in 1,4-dioxane (5 mL) and water (5 mL) was stirred for 2 h at 40° C. Then the mixture was concentrated to 5 mL and adjusted to pH=2 with 2M HCl. The precipitate was filtered and purified by prep-HPLC to give 3-(8-(6-(4,4-dimethylpiperidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (18 mg, 9%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 10.53 (s, 1H), 8.94 (s, 1H), 8.52 (s, 2H), 8.18-8.12 (m, 3H), 7.72 (t, 1H, J=7.8 Hz), 7.57 (t, 1H, J=7.8 Hz), 6.76 (d, 1H, J=7.8 Hz), 6.54 (d, 1H, J=8.1 Hz), 3.59-3.57 (m, 4 h), 1.38-1.36 (m, 4 h), 0.98 (s, 6H). LC-MS: [M+H]+, 443, tR=1.788 min, HPLC: 100% at 214 nm, 100% at 254 nm, tR=6.762 min.

Workup

  1. concentrationThen the mixture was concentrated to 5 mL
  2. filtrationThe precipitate was filtered
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-8f6484cc8a99442392c5dae30b104285
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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