Methyl iodide → HCID 67041997, compound

HRID 717017Notes

Reaction equation

HRID 717017 reaction equation
[CH:1]1([NH:6][C:7]2[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:29]I>O1CCCC1>[CH:1]1([N:6]([CH3:29])[C:7]2[C:8]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67042032HCID 67042032, compound

Product 1

HCID 67041997HCID 67041997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-(cyclopentylamino)-2-phenylquinoxaline-6-carboxylate (214.1 mg, 0.62 mmol, 1.00 equiv) in tetrahydrofuran (10 mL). This was followed by the addition of sodium hydride (246.8 mg, 6.17 mmol, 10.00 equiv, 60%) dropwise with stiffing at 0° C. The resulting solution was stirred for 1 h at room temperature. To this was added a solution of CH3I (1.75 g, 12.32 mmol, 20.00 equiv) in tetrahydrofuran (2 mL) dropwise with stiffing at 0° C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of water. The resulting mixture was concentrated under vacuum. This resulted in 200 mg (crude) of methyl 3-(cyclopentyl(methyl)amino)-2-phenylquinoxaline-6-carboxylate as yellow oil.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customwith stiffing at 0° C
  4. customwith stiffing at 0° C
  5. stirringThe resulting solution was stirred overnight at room temperature
  6. customThe reaction was then quenched by the addition of water
  7. concentrationThe resulting mixture was concentrated under vacuum
  8. customThis resulted in 200 mg (crude) of methyl 3-(cyclopentyl(methyl)amino)-2-phenylquinoxaline-6-carboxylate as yellow oil

Sources & evidence

ORD record
ord-9aeff603767a45e8bd93f5da16c264e7
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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