Hydrochloric Acid → HCID 178507120, compound

HRID 1501366Notes

Reaction equation

HRID 1501366 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[C:19]([C:20]5[CH:24]=[CH:23][NH:22][N:21]=5)=[CH:18][C:17]([C:25]([O:27]C)=[O:26])=[N:16][N:15]4[C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].O.Cl>CO>[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[C:19]([C:20]5[CH:24]=[CH:23][NH:22][N:21]=5)=[CH:18][C:17]([C:25]([OH:27])=[O:26])=[N:16][N:15]4[C:29]=3[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178497280HCID 178497280, compound

Product 1

HCID 178507120HCID 178507120, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-8-(1H-pyrazol-3-yl)imidazo[1,2-b]pyridazine-6-carboxylate that was prepared in a manner analgous to that described for Example 56 (0.19 g, 0.41 mmol) in MeOH (5 mL) was added an aqueous NaOH solution (10% 0.65 mL, 1.64 mmol, 4.0 equiv). The resulting mixture was stirred at room temperature for 48 h. Water 10 mL) was added to the resulting mixture and the pH was adjusted to pH 4 using an aqueous 2N HCl solution. The resulting precipate was collected by filtration, and recrystallized from dimethyl sulfoxide to give 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-8-(1H-pyrazol-3-yl)imidazo[1,2-b]pyridazine-6-carboxylic acid (0.012 g, 6%).

Workup

  1. filtrationThe resulting precipate was collected by filtration
  2. customrecrystallized from dimethyl sulfoxide

Sources & evidence

ORD record
ord-a785d3ad39554dc08c5e1bcad78941f5
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

Loading…