Potassium Iodide → (1S)-1-{2-[(2R)-4-(1,2-Dihydro-5-acenaphthylenyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carboxamide

HRID 2056732Notes

Reaction equation

HRID 2056732 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([N:13]2[CH2:18][CH2:17][NH:16][C@H:15]([CH3:19])[CH2:14]2)=[CH:5][CH:4]=[C:3]3[CH2:2]1.CS(O[CH2:25][CH2:26][C@H:27]1[C:32]2[CH:33]=[CH:34][C:35]([C:37]([NH2:39])=[O:38])=[CH:36][C:31]=2[CH2:30][CH2:29][O:28]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH2:25][CH2:26][C@H:27]4[C:32]5[CH:33]=[CH:34][C:35]([C:37]([NH2:39])=[O:38])=[CH:36][C:31]=5[CH2:30][CH2:29][O:28]4)[C@H:15]([CH3:19])[CH2:14]2)=[CH:5][CH:4]=[C:3]3[CH2:2]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 69307361(3R)-1-(1,2-Dihydro-5-acenaphthylenyl)-3-methylpiperazineHCID 865960122-[(1S)-6-(aminocarbonyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl methanesulfonate

Product 1

HCID 9890237(1S)-1-{2-[(2R)-4-(1,2-Dihydro-5-acenaphthylenyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3R)-1-(1,2-Dihydro-5-acenaphthylenyl)-3-methylpiperazine (0.138 g, 0.55 mmol), 2-[(1S)-6-(aminocarbonyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl methanesulfonate (0.15 g, 0.50 mmol), potassium carbonate (0.138 g, 1.0 mmol), potassium iodide (0.083 g, 1.0 mmol) and acetonitrile (50 mL) were heated under reflux for 1 day with stirring under nitrogen. After cooling to room temperature, the inorganics were filtered off and the solvent evaporated in vacuo. The crude product was purified by preparative LC-MS to give the title compound. M+H=456.

Workup

  1. temperatureunder reflux for 1 day
  2. filtrationthe inorganics were filtered off
  3. customthe solvent evaporated in vacuo
  4. customThe crude product was purified by preparative LC-MS

Sources & evidence

ORD record
ord-ba32c0e3fb5344deb93548bd1d2e5125
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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