Hydrochloric Acid → HCID 86607561, compound

HRID 1987849Notes

Reaction equation

HRID 1987849 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][C:34]=1[N+:35]([O-:37])=[O:36])[C:8]([C:10]1[N:18]2[C:13]([CH:14]=[C:15]([NH:19][CH3:20])[CH:16]=[CH:17]2)=[C:12]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[C:11]=1[CH3:31])=[O:9].[CH3:38]I.Cl>CN(C)C=O.ClCCl>[CH3:20][N:19]([CH3:38])[C:15]1[CH:16]=[CH:17][N:18]2[C:13]([CH:14]=1)=[C:12]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C:11]([CH3:31])=[C:10]2[C:8](=[O:9])[C:7]1[CH:32]=[CH:33][C:34]([N+:35]([O-:37])=[O:36])=[C:5]([O:4][CH3:3])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86607562HCID 86607562, compound

Product 1

HCID 86607561HCID 86607561, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

80 mg (1.67 mmol) of sodium hydride (60% as a dispersion in oil) at room temperature are added in portions to 525 mg (1.11 mmol) of benzyl [3-(3-methoxy-4-nitrobenzoyl)-2-methyl-7-methylaminoindolizin-1-yl]carboxylate in solution in 10 mL of dimethylformamide. After 10 minutes, 138 μL (2.22 mmol) of methyl iodide are added to the reaction mixture. The medium is stirred at 40° C. for 2 hours, poured into a molar solution of hydrochloric acid and then extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The solid obtained is taken up in dichloromethane and filtered. 439 mg of a light orange-coloured solid are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe solid obtained
  6. filtrationfiltered

Sources & evidence

ORD record
ord-8022941317ef4ff9aca82e964d53b306
Source dataset
uspto-grants-2009_06
Patent number
US07553845B2

Reaction notes

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