Hydrochloric Acid → HCID 178437933, compound

HRID 79367Notes

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[C:26]([O:32]C)=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[N:4]=1)[CH3:2].Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.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][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[C:26]([OH:32])=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-(3-ethyl-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (50 mg, 0.11 mmol) and HCl (2 mL, 4M in dioxane) was heated at 80° C. in a sealed vial for 4 hours. The reaction mixture was diluted with ethyl acetate (20 mL) and water (5 mL). Saturated NaHCO3 aqueous solution was added to adjust pH=7. The solution was concentrated under reduced pressure to a solid residue. The residue was dissolved in DCM/MeOH and filtered to remove inorganic impurities. The solution was concentrated under reduced pressure to give the product (48 mg).

Workup

concentrationThe solution was concentrated under reduced pressure to a solid residue
dissolutionThe residue was dissolved in DCM/MeOH
filtrationfiltered
customto remove inorganic impurities
concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-be0173a84a69440eb3c7d347fa254688
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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