Hydrochloric Acid → HCID 131734991, compound

HRID 923490Notes

Reaction equation

HRID 923490 reaction equation
[C:1]([Si:5]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[O:6][CH2:7][C:8]([NH:12][C:13]([C:15]1[N:19]2[CH:20]=[CH:21][CH:22]=[C:23]([O:24][CH2:25][C:26]3[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=3[F:33])[C:18]2=[N:17][C:16]=1[CH3:34])=[O:14])([C:10]#[N:11])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C[Sn]([N:51]=[N+:52]=[N-:53])(C)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.CO>[C:1]([Si:5]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[O:6][CH2:7][C:8]([NH:12][C:13]([C:15]1[N:19]2[CH:20]=[CH:21][CH:22]=[C:23]([O:24][CH2:25][C:26]3[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=3[F:33])[C:18]2=[N:17][C:16]=1[CH3:34])=[O:14])([C:10]1[N:51]=[N:52][NH:53][N:11]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5104973Azido(trimethyl)stannaneHCID 131734988HCID 131734988, compound

Product 1

HCID 131734991HCID 131734991, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 300 mg of N-(1-{[tert-butyl (diphenyl)silyl]oxy}-2-cyanopropan-2-yl)-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 6 ml of toluene was added 240 mg of trimethyltin azide, followed by stirring for 4 hours under heating to reflux. The reaction mixture was left to be cooled to room temperature, and 10 ml of methanol and 10 ml of 1 M hydrochloric acid were then added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was neutralized by the addition of 1 M sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 292 mg of N-[1-{[tert-butyl (diphenyl)silyl]oxy}-2-(2H-tetrazol-5-yl)propan-2-yl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. temperatureunder heating to reflux
  2. waitThe reaction mixture was left
  3. stirringby stirring at room temperature for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. customthe solvent was then evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d48557c7838747adb96a22f5698ac38d
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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