Methyl iodide → HCID 58243374, compound

HRID 2361688Notes

Reaction equation

HRID 2361688 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][CH:9]2[CH2:12][N:11]([C:13]([N:15]3[CH2:21][CH2:20][CH2:19][N:18]([CH:22]4[CH2:25][CH2:24][CH2:23]4)[CH2:17][CH2:16]3)=[O:14])[CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30]I>C1COCC1>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([N:8]([CH:9]2[CH2:12][N:11]([C:13]([N:15]3[CH2:21][CH2:20][CH2:19][N:18]([CH:22]4[CH2:23][CH2:24][CH2:25]4)[CH2:17][CH2:16]3)=[O:14])[CH2:10]2)[CH3:30])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58243412HCID 58243412, compound

Product 1

HCID 58243374HCID 58243374, compoundYield 949.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-N-{1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}benzamide (15 mg, 38 μmol) in THF (2 ml) was added NaH (3 mg of a 60% dispersion in mineral oil, 76 μmol). The reaction was stirred at room temperature for 30 minutes and then MeI (2.6 μmol, 46 μmol) was added. The reaction was heated in a sealed tube at 50° C. for 3 hours and then concentrated at reduced pressure, diluted with dichloromethane (30 ml), washed twice with saturated NaHCO3 (15 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by FCC (DCM/MeOH/NH3 with gradient, 95:5:1 to 90:10:1) to provide the title compound as colourless oil (10 mg, 66%).

Workup

  1. temperatureThe reaction was heated in a sealed tube at 50° C. for 3 hours
  2. concentrationconcentrated at reduced pressure
  3. additiondiluted with dichloromethane (30 ml)
  4. washwashed twice with saturated NaHCO3 (15 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customThe residue was purified by FCC (DCM/MeOH/NH3 with gradient, 95:5:1 to 90:10:1)

Sources & evidence

ORD record
ord-f6c83cf6ed764e9db9df687658f6752f
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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