Hydrochloric Acid → 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylic acid

HRID 79324Notes

Reaction equation

HRID 79324 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([O:26]CC)=[O:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=2)[N:4]=1)[CH3:2].[OH-].[Li+].Cl>C1COCC1.O>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([OH:26])=[O:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67260084ethyl 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylate

Product 1

HCID 672601493-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylic acidYield 101.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

To ethyl 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylate (430 mg, 0.891 mmol; prepared as in Example 23) in THF/H2O (6 mL/1 mL) was added lithium hydroxide (21.3 mg, 0.891 mmol). The reaction mixture was sealed and heated to 70° C. for 2 hours. The mixture was cooled to ambient temperature and HCl (0.45 mL, 4M in dioxane) was added. The mixture was concentrated under reduced pressure to give crude product (410 mg, mixed with LiCl).

Workup

  1. customThe reaction mixture was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-128a828b0fb540d5a9dce1b3cf6df6f8
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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