Water → HCID 21942972, compound

HRID 2216440Notes

Reaction equation

HRID 2216440 reaction equation
[CH3:1][O:2][CH2:3][C:4]([Cl:6])=[O:5].Cl.[C:8]([N:11]1[C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[S:13][CH:12]1[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[O:29][CH2:30][CH2:31][CH2:32][N:33]([CH2:37][CH2:38][OH:39])[CH:34]([CH3:36])[CH3:35])(=[O:10])[CH3:9].C(N(CC)CC)C.O>C(Cl)Cl>[ClH:6].[C:8]([N:11]1[C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[S:13][CH:12]1[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[O:29][CH2:30][CH2:31][CH2:32][N:33]([CH:34]([CH3:35])[CH3:36])[CH2:37][CH2:38][O:39][C:4](=[O:5])[CH2:3][O:2][CH3:1])(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 21942813HCID 21942813, compound

Product 1

HCID 21942972HCID 21942972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methoxyacetyl chloride (0.08 ml, 0.87 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 triethylamine (0.41 ml, 2.90 mmol) and methylene chloride (1.0 ml) under ice-cooling. The mixture was stirred at room temperature for two hours, then water (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. Ethyl acetate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (mobile phase: chloroform/methanol=50/1). The obtained oily matter was dissolved in ethyl acetate (1 ml), and then a 4 N solution (0.2 ml) of hydrogen chloride in ethyl acetate was added thereto under ice-cooling. The mixture was concentrated under reduced pressure to give 340 mg (quantitatively) 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. customEthyl acetate was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (mobile phase: chloroform/methanol=50/1)
  6. dissolutionThe obtained oily matter was dissolved in ethyl acetate (1 ml)
  7. additiona 4 N solution (0.2 ml) of hydrogen chloride in ethyl acetate was added
  8. temperatureunder ice-cooling
  9. concentrationThe mixture was concentrated under reduced pressure
  10. customto give 340 mg (quantitatively) of the target compound

Sources & evidence

ORD record
ord-e54c93fe0b674e4eb6e0a2d9707593f4
Source dataset
uspto-grants-2006_09
Patent number
US07112598B2

Reaction notes

Loading…