Methyl iodide → HCID 21352223, compound

HRID 1250873Notes

Reaction equation

HRID 1250873 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[CH2:7][NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)=[O:10].CI.[C:27](OCC)(=O)C>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[CH2:7][N:8]([CH3:27])[C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 485057HCID 485057, compound

Product 1

HCID 21352223HCID 21352223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (10 mg) in DMF (1 mL) at 0° C. was added a solution of the compound of Example 1 (68 mg, 0.23 mmol) in DMF (1mL). The reaction mixture was stirred at the same temperature for 30 minutes then methyl iodide (20 μL, 0.32 mmol) was added. Reaction mixture was stirred at room temperature overnight. It was then poured into ethyl acetate, washed with water, brine, dried over magnesium sulfate and concentrated to give a white solid. Purification was done using a silica gel column and ethyl acetate as the eluent. 1H NMR (300 MHz; CDCl3): Mixture of rotamers 9.13 (m, 1H); 8.29−8.18 (m, 2H); 7.86 (dd, 1H, J=8.2 and 12 Hz); 7.58−7.11 (complex mixture; 3H); 6.98−6.71 (complex mixture, 2H); 4.91 and 4.85 (2s, 2H) and 3.84 and 3.58 (2 s, 3H); 3.18 and 3.04 (2 s, 3H) ppm.

Workup

  1. customReaction mixture
  2. stirringwas stirred at room temperature overnight
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a white solid
  7. customPurification

Sources & evidence

ORD record
ord-bff77751a8034cfe85e2d543653c371c
Source dataset
uspto-grants-2002_01
Patent number
US06340690B1

Reaction notes

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