Hydrochloric Acid → HCID 18426757, compound

HRID 380169Notes

Reaction equation

HRID 380169 reaction equation
C1OC1C.B(Br)(Br)Br.[CH2:9]([N:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([C:25]#[C:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH:22]=[CH:21][C:20]=2[O:33]C)=[C:15]([NH:35][C:36]([NH:38][C:39]2[C:44]([CH:45]([CH3:47])[CH3:46])=[CH:43][CH:42]=[CH:41][C:40]=2[CH:48]([CH3:50])[CH3:49])=[O:37])[C:14]1=[O:51])[CH2:10][CH2:11][CH3:12].[OH-].[Na+].Cl>C(Cl)Cl>[CH2:9]([N:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([C:25]#[C:26][CH2:27][N:28]([CH2:29][CH3:30])[CH2:31][CH3:32])[CH:22]=[CH:21][C:20]=2[OH:33])=[C:15]([NH:35][C:36]([NH:38][C:39]2[C:40]([CH:48]([CH3:50])[CH3:49])=[CH:41][CH:42]=[CH:43][C:44]=2[CH:45]([CH3:47])[CH3:46])=[O:37])[C:14]1=[O:51])[CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6378Propylene OxideHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 18426758HCID 18426758, compound

Product 1

HCID 18426757HCID 18426757, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of propylene oxide (0.07 ml, 1.04 mmol) in methylene chloride (10 ml) was added BBr3 (0.29 ml, 3.11 mmol) under ice-cooling, and the mixture was stirred for 30 minutes. To the mixture was added N-[1-butyl-2-oxo-4-[2-methoxy-5-{3-(diethylamino)-1-propynyl}phenyl]-1,2-dihydropyridin-3-yl]-N′-(2,6-diisopropylphenyl)urea (303 mg, 0.518 mmol), and the mixture was stirred under reflux for 4 hours. To the reaction solution was added a 10% aqueous sodium hydroxide solution, and the mixture was acidified with 3N hydrochloric acid. The mixture was extracted with chloroform, and the extract was washed with a saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:30) to give the title compound (77 mg, <26%) as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred
  3. temperatureunder reflux for 4 hours
  4. extractionThe mixture was extracted with chloroform
  5. washthe extract was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:30)

Sources & evidence

ORD record
ord-989d789c0956465ea68993ef9f8a34de
Source dataset
uspto-grants-2001_10
Patent number
US06300500B1

Reaction notes

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