Hydrochloric Acid → HCID 178437935, compound

HRID 79302

Reaction equation

HRID 79302 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][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31]C)[N:26]=2)[N:4]=1)[CH3:2].Cl.C([O-])(O)=O.[Na+]>C1COCC1>[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][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[N:26]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67259608N-(3-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 178437935HCID 178437935, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To N-(3-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (210 mg, 0.492 mmol) in THF (6 mL) was added hydrochloric acid (4M in dioxane, 2 mL). The reaction vial was sealed, heated to 80° C. and stirred for 24 hours. The reaction was cooled to ambient temperature and saturated NaHCO3 aqueous solution was added until pH=7. THF and H2O were removed under reduced pressure. The resulting solid was washed with H2O (20 mL) and dried under vacuum to provide the desired product (198 mg).

Workup

  1. customThe reaction
  2. customvial was sealed
  3. temperatureThe reaction was cooled to ambient temperature
  4. customTHF and H2O were removed under reduced pressure
  5. washThe resulting solid was washed with H2O (20 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c5e7b3ae1473447abe4cc9c132cd542a
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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