Methyl iodide → HCID 68109747, compound

HRID 2174640Notes

Reaction equation

HRID 2174640 reaction equation
[H-].[Na+].[CH2:3]1COCC1.[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([C:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21](=[O:29])[CH2:20][N:19]=2)[CH:9]=1.CI>O>[CH3:3][N:22]1[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:18]([C:10]2[CH:9]=[N:8][C:17]3[C:12]([CH:11]=2)=[CH:13][CH:14]=[CH:15][CH:16]=3)=[N:19][CH2:20][C:21]1=[O:29]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67067065HCID 67067065, compound

Product 1

HCID 68109747HCID 68109747, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60% sodium hydride (62.8 mg, 1.57 mmol) was added to 25 mL of THF solution of 5-(3-quinolinyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (0.30 g, 1.04 mmol) at 0° C., followed by stirring at the same temperature for 20 minutes. Moreover, methyl iodide (0.18 g, 1.25 mmol) was added to the resulting solution, followed by bringing back to room temperature and stirring for 12 hours. 20 mL of water was slowly added to the reaction solution to stop the reaction. The resulting solution was extracted twice with 50 mL of ethyl acetate, and the extracted organic layers were mixed, followed by washing with 50 mL of brine and drying with magnesium sulfate. After filtering and concentrating, the resulting residue was purified by silica gel column chromatography to obtain the target compound (0.17 g, yield: 53%), which was slightly yellow amorphous.

Workup

  1. customby bringing back to room temperature
  2. stirringstirring for 12 hours
  3. customthe reaction
  4. extractionThe resulting solution was extracted twice with 50 mL of ethyl acetate
  5. additionthe extracted organic layers were mixed
  6. washby washing with 50 mL of brine
  7. dry with materialdrying with magnesium sulfate
  8. filtrationAfter filtering
  9. concentrationconcentrating
  10. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3102ca51fea24fa48fc07ec1d196717d
Source dataset
uspto-grants-2015_06
Patent number
US09062024B2

Reaction notes

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