Pyridine → HCID 23067484, compound

HRID 2218198Notes

Reaction equation

HRID 2218198 reaction equation
[C:1]([Cl:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:11]([N:14]1[C:18]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:17]=2[S:16][CH:15]1[C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[O:32][CH2:33][CH2:34][CH2:35][N:36]([CH2:40]CO)[CH:37]([CH3:39])[CH3:38])(=[O:13])[CH3:12].N1C=CC=CC=1.[C:49](=O)([O-:51])[OH:50].[Na+]>C(Cl)Cl>[ClH:9].[C:11]([N:14]1[C:18]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:17]=2[S:16][CH:15]1[C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[O:32][CH2:33][CH2:34][CH2:35][N:36]([CH:37]([CH3:39])[CH3:38])[CH2:40][CH:1]([C:49]([OH:51])=[O:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 21942813HCID 21942813, compound

Product 1

HCID 23067484HCID 23067484, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (0.20 ml, 1.20 mmol) was added to a solution of 3-acetyl-6-chloro-2-[2-(3-(N-(2-hydroxyethyl)-N-isopropylamino)-propoxy)-5-methoxyphenyl]benzothiazoline hydrochloride (300 mg, 0.58 mmol) and pyridine (0.39 ml, 4.70 mmol) in methylene chloride (0.5 ml) under ice-cooling. The mixture was stirred at the temperature for two hours, then a saturated aqueous sodium hydrogencarbonate solution (50 ml) was added to the reaction mixture, and the whole was extracted with ethyl acetate (50 ml). The ethyl acetate layer was washed with a 10% aqueous citric acid solution (50 ml) and dehydrated with anhydrous magnesium sulfate, and ethyl acetate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase:ethyl acetate/methanol=10/1). The obtained oily matter was dissolved in ethyl acetate (1 ml), and a 4 N solution (0.5 ml) of hydrogen chloride in ethyl acetate was added thereto under ice-cooling. The mixture was concentrated under reduced pressure to give 211 mg (62%) of the target compound.

Workup

  1. temperaturecooling
  2. extractionthe whole was extracted with ethyl acetate (50 ml)
  3. washThe ethyl acetate layer was washed with a 10% aqueous citric acid solution (50 ml)
  4. customwas evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (mobile phase:ethyl acetate/methanol=10/1)
  6. dissolutionThe obtained oily matter was dissolved in ethyl acetate (1 ml)
  7. additiona 4 N solution (0.5 ml) of hydrogen chloride in ethyl acetate was added
  8. temperatureunder ice-cooling
  9. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7938a425046748a09b871f34139213d5
Source dataset
uspto-grants-2008_08
Patent number
US07410987B2

Reaction notes

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