Chloride → HCID 14368377, compound

HRID 1762213Notes

Reaction equation

HRID 1762213 reaction equation
C(OC([NH:8][C:9]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:10]=1[CH2:11][O:12][C:13]1[C:14]2[N:15]([C:19]([CH2:23][C:24]#[CH:25])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)=O)(C)(C)C.[Cl-]>C(O)C.C(OCC)C>[NH2:8][C:9]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:10]=1[CH2:11][O:12][C:13]1[C:14]2[N:15]([C:19]([CH2:23][C:24]#[CH:25])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 312ChlorideHCID 20042524HCID 20042524, compound

Product 1

HCID 14368377HCID 14368377, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 8-(2-t-butoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (1.04 g) in ethanol (15.5 ml) was added dropwise 25% ethanolichydrogen chloride (8.4 ml) with ice-cooling. After being stirred for 3 hours at ambient temperature, the mixture was diluted with diethyl ether. The resulting precipitates were collected by filtration, treated with a saturated aqueous solution of sodium hydrogen carbonate and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was triturated with diethyl ether to give 8-(2-amino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (0.58 g).

Workup

  1. temperaturecooling
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. additiontreated with a saturated aqueous solution of sodium hydrogen carbonate
  5. extractionextracted with methylene chloride
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-5a55f3d4b6f341758d29cadc5f616e53
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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