Water → HCID 21942932, compound

HRID 2216437Notes

Reaction equation

HRID 2216437 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl.[C:15]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[S:20][CH:19]1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[O:36][CH2:37][CH2:38][CH2:39][N:40]([CH2:44][CH2:45]OC)CCC)(=[O:17])[CH3:16].O>CN(C)C=O>[ClH:27].[C:15]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[S:20][CH:19]1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[O:36][CH2:37][CH2:38][CH2:39][N:40]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:44]([CH3:45])[CH3:1])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 21942959HCID 21942959, compound

Product 1

HCID 21942932HCID 21942932, compoundYield 180%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (299 mg, 2.16 mmol) and ethyl bromoacetate (0.13 ml, 1.13 mmol) were added to a solution of 3-acetyl-6-chloro-2-[2-(3-(N-isopropylamino)propoxy)-5-methoxyphenyl]benzothiazoline (compound described in Example 3) (474 mg, 1.08 mmol) in anhydrous dimethylformamide at room temperature. The mixture was stirred at room temperature for 1.5 hours, water (30 ml) was added to the reaction mixture, and the whole was extracted with diethyl ether (50 ml). The organic layer was washed with water twice and saturated brine successively and dehydrated with anhydrous magnesium sulfate. Diethyl ether was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1). Methanol (2 ml) was added to the obtained oily matter, and a 10% solution (5 ml) of hydrogen chloride in methanol was added thereto with stirring under ice-cooling. The mixture was stirred at the temperature for five minutes, and the solvent was evaporatd under reduced pressure to give 542 mg (90%) of the target compound.

Workup

  1. extractionthe whole was extracted with diethyl ether (50 ml)
  2. washThe organic layer was washed with water twice
  3. customDiethyl ether was evaporated under reduced pressure
  4. customthe obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1)
  5. additionMethanol (2 ml) was added to the obtained oily matter
  6. additiona 10% solution (5 ml) of hydrogen chloride in methanol was added
  7. stirringwith stirring under ice-
  8. temperaturecooling
  9. stirringThe mixture was stirred at the temperature for five minutes

Sources & evidence

ORD record
ord-6b308290177b45b689d64a25550ce7b0
Source dataset
uspto-grants-2006_09
Patent number
US07112598B2

Reaction notes

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