Methyl iodide → HCID 57595435, compound

HRID 1786051Notes

Reaction equation

HRID 1786051 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@H:20]([N:27]([C:35](=[O:37])[CH3:36])[C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH2:19][C@@H:18]2[CH3:38])=[O:16])=[CH:11][CH:10]=1)=[O:7].[H-].[Na+].I[CH3:43]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]([N:8]([C:9]1[CH:10]=[CH:11][C:12]([C:15]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@H:20]([N:27]([C:35](=[O:37])[CH3:36])[C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)[CH2:19][C@@H:18]2[CH3:38])=[O:16])=[CH:13][CH:14]=1)[CH3:43])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68921678HCID 68921678, compound

Product 1

HCID 57595435HCID 57595435, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,4R)-N-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-succinamic acid methyl ester (55 mg, 0.100 mmoles) in DMF was added sodium hydride (60% dispersion in oil). After 30 minutes, iodomethane (16 uL, 0.11 mmoles) was added to the reaction mixture and stirred at room temperature overnight. Reaction was quenched with water and extracted with ethyl acetate. Combined organics were washed with saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Product was purified on silica gel by flash chromatography using 100% ethyl acetate and 90% ethyl acetate/10% methanol to afford (2S,4R)-N-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-N-methyl-succinamic acid methyl ester (16 mg, 26%).

Workup

  1. customReaction
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate
  4. washCombined organics were washed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customProduct was purified on silica gel by flash chromatography

Sources & evidence

ORD record
ord-f87f3573c9554627adb678ba79085bae
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…