Methyl iodide → HCID 58574468, compound

HRID 1619351Notes

Reaction equation

HRID 1619351 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:22][CH2:21][N:20]2[C:11](=[N:12][C:13]3[C:18]([C:19]2=[O:23])=[CH:17][CH:16]=[C:15]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[CH:14]=3)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:36]I>CN(C=O)C>[F:32][C:28]1[CH:27]=[C:26]([C:25]#[C:24][C:15]2[CH:14]=[C:13]3[C:18]([C:19](=[O:23])[N:20]4[CH2:21][CH2:22][CH:8]([N:7]([CH3:36])[C:6](=[O:33])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:9][CH2:10][C:11]4=[N:12]3)=[CH:17][CH:16]=2)[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58574389HCID 58574389, compound

Product 1

HCID 58574468HCID 58574468, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of tert-butyl-3-((3-fluorophenyl)ethynyl)-12-oxo-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-8-ylcarbamate (0.3 g, 0.67 mmol, 1 equiv) and NaH (64.3 mg, 2.68 mmol, 4 equiv) in DMF (15 mL) was added CH3I dropwise. After stirring at rt for 2 hours, the reaction mixture was quenched with water and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the desired product, which was purified by silica gel chromatography. MS (ESI): 462 (MH+).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-add3299288244b918eede1eb4fc8020f
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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