Potassium Carbonate → (S)-1-(4-Chloroquinolin-7-ylmethyl)-4-[3-(5-chlorothiophen-2-yl)-allyl]-3-methylpiperazin-2-one

HRID 1432991Notes

Reaction equation

HRID 1432991 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][C@@H:16]([CH3:20])[C:15]3=[O:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.Br[CH2:23]/[CH:24]=[CH:25]/[C:26]1[S:27][C:28]([Cl:31])=[CH:29][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([CH2:23][CH:24]=[CH:25][C:26]4[S:27][C:28]([Cl:31])=[CH:29][CH:30]=4)[C@@H:16]([CH3:20])[C:15]3=[O:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 217085162-(3-Bromo-(E)-propenyl)-5-chloro-thiopheneHCID 69024355HCID 69024355, compound

Product 1

HCID 54504925(S)-1-(4-Chloroquinolin-7-ylmethyl)-4-[3-(5-chlorothiophen-2-yl)-allyl]-3-methylpiperazin-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-1-(4-chloroquinolin-7-ylmethyl)-3-methylpiperazin-2-one hydrochloride (0.25 g, 1.0 mmol), EXAMPLE 91, is treated with 2-(3-Bromo-(E)-propenyl)-5-chloro-thiophene (0.35 g 1.2 mmol), EXAMPLE 17, and potassium carbonate (0.5 g, 3 mmol). The resulting suspension is sonicated for 10 minutes then stirred vigorously for 16 h at ambient temperature. The reaction mixture is poured into water and extracted with ethyl acetate (2×150 mL). The organic layer is washed with water (4×200 mL), dried over sodium sulfate and concentrated. The residue is chromatographed (3% methanol/methylene chloride) to give the title compound (0.31 g, 0.73 mmol).

Workup

  1. customThe resulting suspension is sonicated for 10 minutes
  2. extractionextracted with ethyl acetate (2×150 mL)
  3. washThe organic layer is washed with water (4×200 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed (3% methanol/methylene chloride)

Sources & evidence

ORD record
ord-a49da500d737467c93305316d887661d
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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