Methyl iodide → HCID 67255412, compound

HRID 1509079Notes

Reaction equation

HRID 1509079 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:27][C:26]4[C:25](=[O:35])[CH:24]([C:36]([O:38][CH3:39])=[O:37])[CH2:23][CH2:22][C:21]=4[N:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:40]C(C)([O-])C.[K+].CI>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[C:28]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:27][C:26]4[C:25](=[O:35])[C:24]([CH3:40])([C:36]([O:38][CH3:39])=[O:37])[CH2:23][CH2:22][C:21]=4[N:20]=3)=[CH:17][CH:18]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 67256387HCID 67256387, compound

Product 1

HCID 67255412HCID 67255412, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 2-(4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)phenyl)-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinoline-6-carboxylate (65 mg, 0.12 mmol) in anhydrous THF (1.0 mL) was cooled to 0° C. under a nitrogen atmosphere, followed by the dropwise addition of potassium tert-butoxide solution (1M in THF, 150 μL, 0.15 mmol). The mixture was stirred at 0° C. for 15 minutes followed by the addition of methyl iodide (10 μL, 0.16 mmol). The reaction mixture was allowed to warm to room temperature and stirred for a further 4 hours. The mixture was diluted with ethyl acetate (2.0 mL), washed with 1M HCl solution (2.0 mL), brine (2×2.0 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give the desired product as a brown solid (54 mg, 83% yield). LCMS (Method A) RT=7.92 min, M+H+=541.18.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for a further 4 hours
  3. washwashed with 1M HCl solution (2.0 mL), brine (2×2.0 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-55525cc9b9204f01b472ccebbb1b3431
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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