Methyl iodide → HCID 57541247, compound

HRID 421745Notes

Reaction equation

HRID 421745 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][N:12]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[S:13]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[CH:36]=[CH:35][C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=4)[CH:28]=[C:23]3[C:22](=[O:37])[C:21]=2[CH:38]=1)(=[O:15])=[O:14].[CH3:45]I.[Cl-].[NH4+]>C1COCC1.O>[CH3:11][N:12]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[S:13]([CH:16]([C:17]1[CH:18]=[CH:19][C:20]2[CH:36]=[CH:35][C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=4)[CH:28]=[C:23]3[C:22](=[O:37])[C:21]=2[CH:38]=1)[CH3:45])(=[O:15])=[O:14]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 25014404HCID 25014404, compound

Product 1

HCID 57541247HCID 57541247, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Lithium bis(trimethylsilyl)amide (1063 μl, 1.063 mmol, 1 M in THF) was added to a solution of N-methyl-1-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-phenylmethanesulfonamide (250 mg, 0.531 mmol) in THF (5.3 mL) at −78° C. After stirring for 30 minutes at −78° C., the solution was warmed to room temperature and then cooled to −78° C. before adding a solution of methyl iodide (100 μl, 1.594 mmol) in THF (3.75 mL) dropwise. After 2 hours, the reaction was warmed to room temperature, acidified with aqueous ammonium chloride (saturated) and water (75 mL), then extracted with dichloromethane (3×100 mL). The combined organic extracts were washed with brine (50 mL×2), dried over anhydrous Na2 SO4, filtered and concentrated under reduced pressure to afford the title compound as a yellow solid. LRMS (APCI) calculated for C27H24N4O3S [M+H]+, 485.2; found 485.1.

Workup

  1. temperaturethe solution was warmed to room temperature
  2. temperaturecooled to −78° C.
  3. waitAfter 2 hours
  4. temperaturethe reaction was warmed to room temperature
  5. extractionextracted with dichloromethane (3×100 mL)
  6. washThe combined organic extracts were washed with brine (50 mL×2)
  7. customdried over anhydrous Na2 SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bca41ad1ade64cfcb1089d3f0062731d
Source dataset
uspto-grants-2012_01
Patent number
US08101603B2

Reaction notes

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