Methyl iodide → HCID 58333556, compound

HRID 2066859Notes

Reaction equation

HRID 2066859 reaction equation
[H-].[Na+].[CH:3]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([O:15][N:16]=[C:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[C:27]([F:29])[C:26]([CH2:30][OH:31])=[CH:25][C:24]=3[F:32])[CH2:19][CH2:18]2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])[CH3:4].CI.[CH3:35]C(OC)(C)C>CN(C=O)C.CO>[CH:3]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([O:15][N:16]=[C:17]2[CH2:18][CH2:19][N:20]([C:23]3[CH:28]=[C:27]([F:29])[C:26]([CH2:30][O:31][CH3:35])=[CH:25][C:24]=3[F:32])[CH2:21][CH2:22]2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 58333373HCID 58333373, compound

Product 1

HCID 58333556HCID 58333556, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (60%, 10 mg, 0.25 mmol) was added to a solution of 48-1 (36 mg, 0.085 mmol) in 0.3 mL of DMF at 0° C. After 10 minutes, methyl iodide in MTBE (2M, 0.6 mL, 1.2 mmol) was added and the reaction was stirred at room temperature for 2 h. The mixture was quenched with water (2 mL) and extracted with 1 mL of ethyl acetate. The organic extract was dried under a stream of nitrogen and the residue was purified by preparative TLC(eluent: 30% EtOAc in hexane) to afford 49-1: LC-MS 408.1 (MH+-MeOH), tR=8.77 (Method 2). EC50: 265 nM.

Workup

  1. customThe mixture was quenched with water (2 mL)
  2. extractionextracted with 1 mL of ethyl acetate
  3. extractionThe organic extract
  4. customwas dried under a stream of nitrogen
  5. customthe residue was purified by preparative TLC(eluent
  6. custom30% EtOAc in hexane) to afford 49-1

Sources & evidence

ORD record
ord-49f27fd2b9744bcab7fb66ea205b383e
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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