Methyl iodide → HCID 57852693, compound

HRID 1890152Notes

Reaction equation

HRID 1890152 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][OH:21])[C:10]=2[C:9]2[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=2[S:7]1)=[O:5])[CH3:2].[OH-].[K+].I[CH3:31]>CS(C)=O>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][O:21][CH3:31])[C:10]=2[C:9]2[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=2[S:7]1)=[O:5])[CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 57852687HCID 57852687, compound

Product 1

HCID 57852693HCID 57852693, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of intermediate iv (from the synthesis described in Example 15) (60 mg, 0.158 mmol) in anhydrous DMSO 3 ml was added potassium hydroxide (84 mg, 1.58 mmol) and iodomethane (1.58 mmol, 0.12 ml) at room temperature. The mixture was then stirred under nitrogen for 30 minutes. The reaction was poured onto water 50 ml, extracted with dichloromethane 2×20 ml, washed with brine 2×20 ml. The organic was dried (MgSO4) and removed in vacuo. The residue was recrystallised from ethylacetate/hexane. The product was filtered and dried under vacuum to give a yellow solid 34 mg. Yield: 55%.

Workup

  1. additionThe reaction was poured onto water 50 ml
  2. extractionextracted with dichloromethane 2×20 ml
  3. washwashed with brine 2×20 ml
  4. dry with materialThe organic was dried (MgSO4)
  5. customremoved in vacuo
  6. customThe residue was recrystallised from ethylacetate/hexane
  7. filtrationThe product was filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-902f983b265f4ac88a638756eda84e51
Source dataset
uspto-grants-2013_08
Patent number
US08506932B2

Reaction notes

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