Pyridine → HCID 21942945, compound

HRID 2216438Notes

Reaction equation

HRID 2216438 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].Cl.[C:9]([N:12]1[C:16]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=2[S:14][CH:13]1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[O:30][CH2:31][CH2:32][CH2:33][N:34](CCO)[CH:35]([CH3:37])[CH3:36])(=[O:11])[CH3:10].N1C=CC=CC=1>C(=O)([O-])O.[Na+]>[ClH:21].[C:5]([O:4][CH2:1][CH2:2][N:34]([CH2:33][CH2:32][CH2:31][O:30][C:23]1[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:22]=1[CH:13]1[N:12]([C:9](=[O:11])[CH3:10])[C:16]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=2[S:14]1)[CH:35]([CH3:36])[CH3:37])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21942813HCID 21942813, compound

Product 1

HCID 21942945HCID 21942945, compoundYield 171.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Acetic anhydride (0.26 ml, 2.91 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) in pyridine (0.47 ml, 5.80 mmol) under ice-cooling, and then the mixture was stirred at room temperature for two hours. 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 saturated brine (50 ml) and dehydrated with anhydrous magnesium sulfate, and ethyl acetate was evaporated under reduced pressure. The obtained oily matter was dissolved in ethyl acetate (1 ml), and then a 4 N solution (0.5 ml) of hydrogen chloride in ethyl acetate. The mixture was concentrated under reduced pressure to give 277 mg (92%) 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 saturated brine (50 ml)
  4. customwas evaporated under reduced pressure
  5. dissolutionThe obtained oily matter was dissolved in ethyl acetate (1 ml)
  6. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7f5c7abd7a2a43ef819c5eec63a8b6ad
Source dataset
uspto-grants-2006_09
Patent number
US07112598B2

Reaction notes

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