Methyl iodide → HCID 59722654, compound

HRID 1664848Notes

Reaction equation

HRID 1664848 reaction equation
[H-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@H:11]1[CH2:17][N:16]2[C:18]([CH2:21][OH:22])=[CH:19][N:20]=[C:15]2[C@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:13][CH2:12]1.I[CH3:32]>O1CCCC1>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@H:11]1[CH2:17][N:16]2[C:18]([CH2:21][O:22][CH3:32])=[CH:19][N:20]=[C:15]2[C@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59722709HCID 59722709, compound

Product 1

HCID 59722654HCID 59722654, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 25.0 mg, 0.61 mmol) was added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-(hydroxymethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (160 mg, 0.41 mmol) and iodomethane (51.0 μL, 0.81 mmol) in tetrahydrofuran (2 mL) at 0° C. After 3 h, the reaction was quenched with water and the mixture was extracted with dichloromethane (3×). The organic layer was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (75 mg). MS 408.2 (M+1).

Workup

  1. customthe reaction was quenched with water
  2. extractionthe mixture was extracted with dichloromethane (3×)
  3. washThe organic layer was washed with water, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-7e0de91b260a49d5ac474dddf10cbd54
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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