Methyl iodide → HCID 11527262, compound

HRID 577785Notes

Reaction equation

HRID 577785 reaction equation
[H-].[Na+].[F:3][C:4]([F:38])([F:37])[C:5]1[CH:6]=[C:7]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:8][NH:9][CH2:10][C:11]1[C:12]([N:21]([CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:22][CH3:23])=[N:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.[C:39](=[S:41])=[S:40].[CH3:42]I>C1COCC1.O>[CH3:42][S:40][C:39](=[S:41])[N:9]([CH2:8][C:7]1[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=[C:5]([C:4]([F:37])([F:3])[F:38])[CH:6]=1)[CH2:10][C:11]1[C:12]([N:21]([CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:22][CH3:23])=[N:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 58689767HCID 58689767, compound

Product 1

HCID 11527262HCID 11527262, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (0.023 g, 0.98 mmol) in dry THF (15 mL) at 0° C., in a 25 mL round bottom flask, was added {3-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-quinolin-2-yl}-cyclopentylmethyl-ethyl-amine (0.25 g, 0.44 mmol), obtained in step (iv) of Example 35. This reaction mixture was stirred for 10 minutes at the same temperature, carbon disulphide (0.112 g, 0.98 mmol) was added dropwise, followed by the addition of methyl iodide (0.208 g, 1.47 mmol). The reaction was allowed to reach RT and stirring was continued for 0.5 h. Water was then added to the reaction, which was then extracted with ethyl acetate. The combined organic layer was washed with brine solution and dried over sodium sulfate. The solvent was evaporated to afford the title compound (0.250 g), yield: 87%, of purity 98.59% (HPLC: Symmetry Shield RP8, [0.01M KH2PO4:CH3CN], 217 nM, Rt 12.221 min).

Workup

  1. customobtained in step (iv) of Example 35
  2. additionwas added dropwise
  3. customto reach RT
  4. extractionwas then extracted with ethyl acetate
  5. washThe combined organic layer was washed with brine solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-04e05425a1d5498fa92b29440c125f73
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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