Methyl iodide → HCID 178503969, compound

HRID 552936Notes

Reaction equation

HRID 552936 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]([NH:20]C(=O)C4C=CC=CC=4)=[S:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.I[CH3:30]>CC(C)=O>[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]([S:20][CH3:30])=[NH:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 15951266HCID 15951266, compound

Product 1

HCID 178503969HCID 178503969, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 64 (0.2 g, 0.698 mmol) in acetone (10 mL) was treated with iodomethane (0.26 mL, 4.189 mmol) at room temperature and the resulting solution was refluxed for over night (14 h). The reaction was brought to room temperature and solvent was evaporated. The crude was diluted with sat. NaHCO3 solution (10 mL) and compound was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layer was washed with brine (10 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 74 (0.04 g, 19%) as a solid. mp 260-162° C.; 1H NMR (DMSO-d6) δ 2.29 (s, 3H), 2.33 (s, 3H), 2.50-2.59 (m, 4H), 3.06 (brs, 2H), 6.01 (s, 1H), 6.64 (brs, 1H), 7.22-7.30 (m, 3H), 10.91 (s, 1H); ESI-MS m/z (%): 301 (M+, 36), 285 (55), 258 (66), 242 (100).

Workup

  1. temperaturethe resulting solution was refluxed for over night (14 h)
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. additionThe crude was diluted with sat. NaHCO3 solution (10 mL) and compound
  5. extractionwas extracted into CH2Cl2 (2×20 mL)
  6. washThe combined CH2Cl2 layer was washed with brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. customSolvent was evaporated
  9. customcrude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-afd3ae79a2ae41cba7a0a136d79cc27b
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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