Methyl iodide → HCID 50992394, compound

HRID 1405503Notes

Reaction equation

HRID 1405503 reaction equation
[C:1]1([C:7]2[C:16]([N:17]3[CH2:22][CH2:21][CH:20]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:19][CH2:18]3)=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:30]([O:32]C)=[O:31])[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:36]I>O1CCCC1>[CH3:36][N:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:20]1[CH2:19][CH2:18][N:17]([C:16]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:8][C:9]3[C:14]([N:15]=2)=[CH:13][C:12]([C:30]([OH:32])=[O:31])=[CH:11][CH:10]=3)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67041984HCID 67041984, compound

Product 1

HCID 50992394HCID 50992394, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 2-phenyl-3-(4-(phenylamino)piperidin-1-yl)quinoxaline-6-carboxylate (297.4 mg, 0.68 mmol, 1.00 equiv) in tetrahydrofuran (16 mL). Then sodium hydride (163 mg, 6.79 mmol, 10.00 equiv) and CH3I (964 mg, 6.79 mmol, 10.00 equiv) was added. The resulting solution was stirred for 2 days at room temperature. The reaction was then quenched by the addition of water. The resulting aqueous solution was extracted with 5×30 mL of dichloromethane. The organic layers were combined and concentrated under vacuum. The crude product (150 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed): Column, SunFire Prep C18, 19*150 mm 5 um; mobile phase, water with 0.05% TFA and CH3CN (25% CH3CN up to 60% in 6 min, up to 100% in 1 min); Detector, UV 254 nm 30 mg of product was obtained. This resulted in 30 mg (10%) of 3-(4-(methyl(phenyl)amino)piperidin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of water
  3. extractionThe resulting aqueous solution was extracted with 5×30 mL of dichloromethane
  4. concentrationconcentrated under vacuum
  5. customThe crude product (150 mg) was purified by Prep-HPLC with the following conditions (AGILENT Pre-HPLC (UV-Directed)
  6. waitmobile phase, water with 0.05% TFA and CH3CN (25% CH3CN up to 60% in 6 min
  7. waitup to 100% in 1 min)

Sources & evidence

ORD record
ord-5f40acff2a3849a69370933ecd406f00
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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