1,3-Dimethyl-2-imidazolidinone → HCID 58306650, compound

HRID 1909855Notes

Reaction equation

HRID 1909855 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]2[CH2:26][CH2:25][CH2:24][CH2:23][C:6]=2[C:7]=1[C:8]([NH:10][C@H:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)[CH3:12])=[O:9].CN1CCN(C)C1=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=1>O>[Cl:49][C:46]1[CH:47]=[CH:48][C:43]([CH2:42][N:2]([CH3:1])[C:3]2[S:4][C:5]3[CH2:26][CH2:25][CH2:24][CH2:23][C:6]=3[C:7]=2[C:8]([NH:10][C@H:11]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[CH3:12])=[O:9])=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 58306597HCID 58306597, compound

Product 1

HCID 58306650HCID 58306650, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 4-[(1S)-1-({[2-(methylamino)-4,5,6,7-tetrahydro-1-benzothien-3-yl]carbonyl}amino)ethyl]benzoate (0.41 g) was added 1,3-dimethyl-2-imidazolidinone (4.0 mL), and potassium carbonate (0.30 g) and 1-(bromomethyl)-4-chlorobenzene (0.34 g) were added thereto under ice-cooling, followed by stirring at 50° C. overnight. The reaction mixture was cooled to room temperature, and then water (50 mL) was added thereto, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate: 15/1-4/1) to obtain methyl 4-{(1S)-1-[({2-[(4-chlorobenzyl)(methyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]ethyl}benzoate (0.15 g).

Workup

  1. additionwere added
  2. temperatureunder ice-cooling
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe obtained organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate: 15/1-4/1)

Sources & evidence

ORD record
ord-74a27b1fcd3a426cb357289770bbed90
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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