Lithium iodide → HCID 71284278, compound

HRID 1481750Notes

Reaction equation

HRID 1481750 reaction equation
C(OC([N:8]1[CH2:45][CH2:44][N:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:19]4[N:20](CC5C=CC(OC)=CC=5OC)[C:21](=[O:32])[C:22]([C:28]([O:30]C)=[O:29])=[C:23]([OH:27])[C:24]=4[CH2:25][CH3:26])=[CH:16][C:17]=3[CH:18]=[C:10]2[CH2:9]1)=O)(C)(C)C.[I-].[Li+]>CCOC(C)=O>[CH2:25]([C:24]1[C:23]([OH:27])=[C:22]([C:28]([OH:30])=[O:29])[C:21](=[O:32])[NH:20][C:19]=1[C:15]1[CH:14]=[CH:13][C:12]2[N:11]3[CH2:44][CH2:45][NH:8][CH2:9][C:10]3=[CH:18][C:17]=2[CH:16]=1)[CH3:26]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 71284294HCID 71284294, compound

Product 1

HCID 71284278HCID 71284278, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl-8-(1-(2,4-dimethoxybenzyl)-3-ethyl-4-hydroxy-5-(methoxycarbonyl)-6-oxo-1,6-dihydropyridin-2-yl)-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate (0.5 g, 0.8 mmol) in EtOAc (8 mL) was added lithium iodide (0.33 g, 2.4 mmol). The solution was heated at 60° C. for 1.5 h then cooled to room temperature and diluted with EtOAc (20 mL). The reaction mixture was washed with 1M HCl (20 mL), 10% Na2S2O3 (20 mL), and brine (20 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated. To the crude residue was added TIPS-H (1 mL) and TFA (1 mL), and the reaction mixture was heated at 60° C. for 1 h. The reaction mixture was allowed to cool to room temperature and the solvents were removed in vacuo. To the crude residue was added HCl/Et2O (1 mL, 2.0 M) and the precipitate was collected by filtration to afford the title compound as a light brown solid (60 mg, 21%).

Workup

  1. temperaturethen cooled to room temperature
  2. washThe reaction mixture was washed with 1M HCl (20 mL), 10% Na2S2O3 (20 mL), and brine (20 mL)
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionTo the crude residue was added TIPS-H (1 mL) and TFA (1 mL)
  7. temperaturethe reaction mixture was heated at 60° C. for 1 h
  8. temperatureto cool to room temperature
  9. customthe solvents were removed in vacuo
  10. additionTo the crude residue was added HCl/Et2O (1 mL, 2.0 M)
  11. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7e5c405fcfb644a5ba98216b5ea70d5b
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

Loading…