Hydrochloric Acid → HCID 67259719, compound

HRID 79440Notes

Reaction equation

HRID 79440 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]([NH:20][C:21]4[CH:29]=[CH:28][CH:27]=[C:26]5[C:22]=4[C:23]([CH2:38][CH3:39])=[N:24][N:25]5[CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[N:32]=4)=[O:19])=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH2:4][O:3]1.[ClH:41]>O.FC(F)(F)C(O)=O.O1CCOCC1.C(OCC)C.ClCCl.CO>[ClH:41].[ClH:41].[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][N:12]2[C:15]([C:18]([NH:20][C:21]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:22]=3[C:23]([CH2:38][CH3:39])=[N:24][N:25]4[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[N:32]=3)=[O:19])=[CH:16][N:17]=[C:11]2[CH:10]=1

Participants

9

Reactant 2

HCID 313Hydrochloric AcidHCID 672594837-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67259719HCID 67259719, compound

Reagents, catalysts & solvents 6

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (77 mg, 0.142 mmol) in water (4 mL), trifluoroacetic acid (4 mL) and 1,4-dioxane (1 mL) was stirred for 1 hour at ambient temperature. The mixture was concentrated under reduced pressure to give a residual oil. The oil was dissolved in a mixture of diethyl ether, dichloromethane and methanol. A solution of hydrogen chloride (0.5 mL; 4M in 1,4-dioxane) was added. The mixture was concentrated under reduced pressure and placed under high vacuum for 16 hours to provide 7-(2,3-dihydroxypropoxy)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride (74 mg) as a beige solid. MS (APCI), positive scan, m/z=501.2 (M+H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a residual oil
  3. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4efeee96c85e4c7b82023777f20afd59
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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