Methyl iodide → HCID 59323262, compound

HRID 2390061Notes

Reaction equation

HRID 2390061 reaction equation
[CH3:1][CH:2]([S:4]([NH:7][C:8]1[CH:9]=[C:10]([CH:41]=[CH:42][CH:43]=1)[CH2:11][N:12]([CH2:20][CH2:21][N:22]1[CH:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:40])[CH:28]=2)[CH2:23]1)C(=O)OC(C)(C)C)(=[O:6])=[O:5])[CH3:3].[H-].[Na+].IC.[C:48](=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:48][N:7]([S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])[C:8]1[CH:9]=[C:10]([CH:41]=[CH:42][CH:43]=1)[CH2:11][NH:12][CH2:20][CH2:21][N:22]1[CH:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:40])[CH:28]=2)[CH2:23]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 59323157HCID 59323157, compound

Product 1

HCID 59323262HCID 59323262, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8.7 mg of tert-butyl 3-(2-propyl sulfonylamino)benzyl-[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethyl]carbamate obtained in Example 131-a) was dissolved in 1 mL of THF, and 0.7 mg of sodium hydride was added thereto under ice-cooling, followed by stirring for 15 minutes. 2.6 mg of iodomethane was added thereto, followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction liquid was under ice-cooling, and a saturated aqueous sodium bicarbonate solution and ethyl acetate were added thereto. The organic layer was separated, the aqueous layer was further extracted by addition of ethyl acetate, and the organic layer was combined and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the solvent was removed by evaporation to obtain 10.0 mg of a crude composition. The crude composition was purified by PLC to obtain 6.3 mg (yield 71%) of a desired product.

Workup

  1. temperatureunder ice-cooling
  2. stirringby stirring at room temperature for 3 hours
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. temperaturecooling
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was further extracted by addition of ethyl acetate
  8. washwashed with saturated brine
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customthe solvent was removed by evaporation
  12. customto obtain 10.0 mg of a crude composition
  13. customThe crude composition was purified by PLC

Sources & evidence

ORD record
ord-b73b516d4de744a9beb8df8174de3c0e
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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