Lithium Hydroxide → 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carboxylic acid

HRID 1925119Notes

Reaction equation

HRID 1925119 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]4[N:15]([CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[N:19]=4)[N:16]=3)[C:6]=2[CH:25]=1.[Li+].[OH-]>O.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]4[N:15]([CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=4)[N:16]=3)[C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66633612ethyl 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carboxylate

Product 1

HCID 592332496-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carboxylic acidYield 77.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of ethyl 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carboxylate 13A (5 g, 12.46 mmol) in 10% H2O/MeOH (200 mL), LiOH (0.597 g, 24.92 mmol) was added. The reaction was stirred at ambient temperature for 18 hrs and then concentrated to remove the MeOH. H2O (100 mL) was added and the pH was adjusted to 4 with concentrated HCl. The resulting solid was collected by filtration, rinsed with water followed by EtOAc, and dried in vacuum over P2O5 to provide the title compound, 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carboxylic acid 13B (3.6 g 9.65 mmol, 77%). The filtrate was extracted with EtOAc (3×150 mL) and the organics were combined, dried with MgSO4, filtered and concentrated to dryness to give an additional 0.6 g of product. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.24 (s, 2 H) 7.24 (d, J=9.35 Hz, 1 H) 7.58 (dd, J=8.84, 1.77 Hz, 1 H) 8.04-8.14 (m, 2H) 8.32 (d, J=1.01 Hz, 1 H) 8.47 (s, 1 H). MS:m/z 373.2 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customto remove the MeOH
  3. additionH2O (100 mL) was added
  4. filtrationThe resulting solid was collected by filtration
  5. washrinsed with water
  6. dry with materialdried in vacuum over P2O5

Sources & evidence

ORD record
ord-d9d9cb74524148b6be29eadf49226c8d
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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