Sodium Hydroxide → Sodium 3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate

HRID 1755304Notes

Reaction equation

HRID 1755304 reaction equation
[OH-].[Na+:2].[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]1[N:14]=[C:13]([NH:15][C:16]2[C:17]3[N:18]([CH:31]=[CH:32][N:33]=3)[N:19]=[C:20]([C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=[O:26])[CH:21]=2)[CH:12]=[CH:11][CH:10]=1>O>[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]1[N:14]=[C:13]([NH:15][C:16]2[C:17]3[N:18]([CH:31]=[CH:32][N:33]=3)[N:19]=[C:20]([C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([O-:27])=[O:26])[CH:21]=2)[CH:12]=[CH:11][CH:10]=1.[Na+:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 715255203-(8-(6-(2-Methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid

Product 1

HCID 71525523Sodium 3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoateYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of NaOH in water (0.05 mol/L, 1.2 mL) was added to 3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (25 mg, 0.06 mmol) and the mixture stirred until the solid was completely dissolved. The solution was concentrated in vacuo to give sodium 3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (20 mg, 76%) as a white solid. 1H NMR (300 MHz, D2O): δ 7.98-7.77 (m, 2H), 7.55-7.38 (m, 2H), 7.26-7.05 (m, 3H), 6.80 (brs, 1H), 5.50 (brs, 1H), 5.41-5.33 (m, 1H), 3.39 (brs, 1H), 2.91 (brs, 1H), 2.63 (brs, 1H), 1.58-1.30 (m, 4 h), 0.60 (s, 3H).

Workup

  1. dissolutionwas completely dissolved
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-4f342276780c49e2abf59aa8a5d3af54
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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