Methyl iodide → HCID 66665424, compound

HRID 406176Notes

Reaction equation

HRID 406176 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:10]=[C:11]3[C:16](=[N:17][C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:15][CH:14]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33]C)=[O:31])[CH2:13][CH2:12]3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH3:36]>CN(C=O)C>[CH3:36][N:15]1[C:16]2[C:11](=[CH:10][C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:17]=2)[CH2:12][CH2:13][CH:14]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 123671351HCID 123671351, compound

Product 1

HCID 66665424HCID 66665424, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of sodium hydride (61.1 mg of a 60% mixture in mineral oil, 1.528 mmol) in dry DMF (5 ml) under N2 was treated with a solution of rac-ethyl 6-(6,7-diphenyl-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl)hexanoate (step 3) (131 mg, 0.306 mmol) in DMF (5 ml). After 30 mins at room temperature iodomethane (0.096 ml, 1.528 mmol) was added and stirring continued for 5 h. The mixture was partitioned between DCM (50 ml) and water (50 ml) and the aqueous portion was separated and extracted with DCM (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-30% EtOAc in iso-hexane afforded a mixture of the title products as a colourless oil;

Workup

  1. customThe mixture was partitioned between DCM (50 ml) and water (50 ml)
  2. customthe aqueous portion was separated
  3. extractionextracted with DCM (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by chromatography on silica eluting with 0-30% EtOAc in iso-hexane
  9. customafforded

Sources & evidence

ORD record
ord-fdac53cbc927484ca4c819890bcc08d1
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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