Methyl iodide → HCID 178480028, compound

HRID 2047542Notes

Reaction equation

HRID 2047542 reaction equation
[N:1]1([C@H:7]2[CH2:10][C@H:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([C:20]5[CH:21]=[N:22][NH:23][CH:24]=5)[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].I[CH3:28]>CN(C=O)C>[CH3:28][N:23]1[CH:24]=[C:20]([C:18]2[CH:17]=[CH:16][C:14]3[N:15]=[C:11]([C@H:9]4[CH2:8][C@H:7]([N:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[CH2:10]4)[S:12][C:13]=3[CH:19]=2)[CH:21]=[N:22]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178419852HCID 178419852, compound

Product 1

HCID 178480028HCID 178480028, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The product of Example 51B (34.0 mg, 0.10 mmole) was dissolved in DMF (2 ml) and then cooled to 0° C. NaH (60%, 44.0 mg, 1.1 mmol) was added under N2, and the reaction was stirred at 0° C. for 0.5 hours. Iodomethane (6.8 μl, 0.11 mmole) was added, and the reaction mixture was stirred at 0° C. for 1 hour, and then slowly raised to room temperature. The mixture was quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane (4×5 ml). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the crude product which was purified by column chromatography (10% methanol in dichloromethane) to give 23.8 mg (67.6%) of title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.94 (d, J=8.48 1H) 7.93 (d, J=2.03 1H) 7.80 (s, 1H) 7.66, (s, 1H) 7.56 (dd, J=8.48, 2.03 1H) 3.80 (s, 3H) 3.87 (m, 1H) 3.27 (m, 1H) 2.38-2.62 (m, 4H) 1.49-1.76 (m, 6H). MS: (M+H)+=353.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 1 hour
  2. temperatureslowly raised to room temperature
  3. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  4. extractionextracted with dichloromethane (4×5 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product which
  10. customwas purified by column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-97c5224328484f62a457b4a9f3f5379b
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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