Iodoethane → HCID 70560981, compound

HRID 1477937Notes

Reaction equation

HRID 1477937 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([C:11]2[N:12]=[N:13][NH:14][N:15]=2)[CH2:9][CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:37][CH3:38]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)([C:11]2[N:12]=[N:13][N:14]([CH2:37][CH3:38])[N:15]=2)[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 68175420HCID 68175420, compound

Product 1

HCID 70560981HCID 70560981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from Step B (65 mg, 0.151 mmol), K2CO3 (41.7 mg, 0.302 mmol) and iodoethane (30.8 mg 0.181 mmol) in DMF (1 mL) was stirred at 80° C. overnight. The volatile was evaporated. The residue was extracted with ethyl acetate (50 mL). The organic layer was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with PE/EA (5/1 to 1/1, v/v) to afford the title compound as a yellow solid. LC/MS m/z=459.0 [M+H]+.

Workup

  1. customThe volatile was evaporated
  2. extractionThe residue was extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with PE/EA (5/1 to 1/1

Sources & evidence

ORD record
ord-60f03c85754d4e4a9e9fe73d0b799444
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

Loading…