Iodoethane → HCID 178477467, compound

HRID 552933Notes

Reaction equation

HRID 552933 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([NH2:20])=[S:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.I[CH2:22][CH3:23]>CC(C)=O>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([S:19][CH2:22][CH3:23])=[NH:20])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 57474455HCID 57474455, compound

Product 1

HCID 178477467HCID 178477467, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 65 (0.2 g, 0.698 mmol) in acetone (10 mL) was treated with iodoethane (0.33 mL, 4.189 mmol) at room temperature and the resulting solution was refluxed for 4 h. The reaction was brought to room temperature, and solvent was evaporated. The crude was diluted with sat. NaHCO3 solution (20 mL) and compound was extracted into CH2Cl2 (3×20 mL). The combined CH2Cl2 layer was washed with brine (15 mL) and dried (Na2SO4). Evaporation of solvent and purification of crude by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 66 (0.055 g, 25%) as a solid. mp 77-79° C.; 1H NMR (DMSO-d6) δ 1.20-1.30 (m, 3H), 2.28 (s, 3H), 2.50-2.57 (m, 4H), 2.90-2.96 (m, 2H), 3.02-3.06 (m, 2H), 5.98-6.04 (m, 2H), 6.60-6.63 (m, 1H), 7.17-7.35 (m, 4H), 10.90 (s, 1H); ESI-MS m/z (%):: 315 (M+, 66), 311 (78), 249 (100).

Workup

  1. temperaturethe resulting solution was refluxed for 4 h
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. additionThe crude was diluted with sat. NaHCO3 solution (20 mL) and compound
  5. extractionwas extracted into CH2Cl2 (3×20 mL)
  6. washThe combined CH2Cl2 layer was washed with brine (15 mL)
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of solvent and purification of crude by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-eba4bde071cb4a9e8cdc6ee2e9b7471c
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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