Iodoethane → HCID 57595398, compound

HRID 1786074Notes

Reaction equation

HRID 1786074 reaction equation
[CH3:1][O:2][C:3](=[O:39])[NH:4][CH2:5][CH2:6][CH2:7][O: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.[H-].[Na+].[CH2:42](I)[CH3:43]>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3](=[O:39])[N:4]([CH2:5][CH2:6][CH2:7][O: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)[CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 57595382HCID 57595382, compound

Product 1

HCID 57595398HCID 57595398, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

(2S,4R)-[3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propyl]-carbamic acid methyl ester (41 mg, 0.074 mmol) was dissolved in THF/DMF (10:1, 3 mL). To this solution was added Sodium Hydride (2 mg, 0.089 mmol), followed by ethyl iodide (14 mg, 0.089 mmol). The reaction was stirred at room temperature for 7 hours and was quenched by adding 1 mL of water. The mixture was concentrated under reduced pressure and dissolved in DCM (15 mL). The reaction mixture was washed with sat. aq. NaHCO3 (15 mL), water (15 mL) and brine (15 mL). The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (5/95 ethyl acetate/hexane—50/50 ethyl acetate/hexane gradient) to afford slightly yellow solid product (15 mg, 35%).

Workup

  1. customwas quenched
  2. additionby adding 1 mL of water
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutiondissolved in DCM (15 mL)
  5. washThe reaction mixture was washed with sat. aq. NaHCO3 (15 mL), water (15 mL) and brine (15 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (5/95 ethyl acetate/hexane—50/50 ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-17331d12cad54a429005a613b8ad811b
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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