Hydrochloric Acid → HCID 118308737, compound

HRID 923520Notes

Reaction equation

HRID 923520 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH:26]3[CH2:30][O:29]C(C)(C)[O:27]3)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.O1CCOCC1.Cl.C(=O)([O-])O.[Na+]>CO>[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH:26]([OH:27])[CH2:30][OH:29])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 90192600HCID 90192600, compound

Product 1

HCID 118308737HCID 118308737, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 273 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)benzyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide, 3 ml of dioxane, and 3 ml of methanol was added 6 ml of 1 M hydrochloric acid under ice-cooling, followed by stirring at room temperature for 16 hours. The reaction mixture was ice-cooled and 0.6 g of sodium hydrogen carbonate was added thereto in small portions to make the mixture weakly basic. The precipitated solid was collected by filtration and washed with water to obtain 236 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[2-(1,2-dihydroxyethyl)benzyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-ceb4012737444af0929b49d6ae1a6e0e
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…