Methyl iodide → HCID 88151531, compound

HRID 324501Notes

Reaction equation

HRID 324501 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([C:16]3[C:17]([S:23]C)=[N:18][C:19](=[O:22])[NH:20][CH:21]=3)[C:10]3[N:11]=[C:12]([CH3:14])[S:13][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:25]=1.CI.[CH3:28]C(C)([O-])C.[K+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([C:16]3[C:17](=[S:23])[NH:18][C:19](=[O:22])[N:20]([CH3:28])[CH:21]=3)[C:10]3[N:11]=[C:12]([CH3:14])[S:13][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:25]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178503574HCID 178503574, compound

Product 1

HCID 88151531HCID 88151531, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of example 39 step (i) (0.1 g) together with methyl iodide (0.040 ml) and a 1M solution of potassium tert-butoxide in tetrahydrofuran (0.52 ml) in N,N-dimethylformamide (10 ml) was heated at 80° C. for 2 h. The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated aqueous ammonium chloride and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated. The crude product was purified by chromatography eluting with 5% ethanol in ethyl acetate to give a yellow oil (86 mg). This material was dissolved in a saturated blue solution of sodium hydrosulphide in N,N-dimethylformamide (3 ml) and heated at 80° C. for 3 h. The reaction mixture was cooled, diluted with dichloromethane and washed with water. The organic phase was dried over magnesium sulphate, filtered and evaporated. The crude product was purified by chromatography eluting with 30% isohexane in ethyl acetate to give the title compound as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated aqueous ammonium chloride and brine
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by chromatography
  7. washeluting with 5% ethanol in ethyl acetate

Sources & evidence

ORD record
ord-efd569c4efad40118f7a331b419c65ac
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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