Methyl iodide → HCID 117667407, compound

HRID 712730Notes

Reaction equation

HRID 712730 reaction equation
[K+].[C:2]([N:5]1[C:14]2[N:13]=[CH:12][C:11]([C:15]3[CH:23]=[N:22][CH:21]=[C:20]([F:24])[C:16]=3[C:17]([O-:19])=[O:18])=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=[O:4])[NH2:3].IC.[C:27](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:27][O:18][C:17](=[O:19])[C:16]1[C:20]([F:24])=[CH:21][N:22]=[CH:23][C:15]=1[C:11]1[CH:12]=[N:13][C:14]2[N:5]([C:2](=[O:4])[NH2:3])[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 117667182HCID 117667182, compound

Product 1

HCID 117667407HCID 117667407, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a vial is added 3-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-5-fluoro-isonicotinic acid potassium salt (100 mg, 0.28 mmol) in 2 ml of DMF, followed by the addition of iodomethane (48 mg, 0.34 mmol) and potassium carbonate (47 mg, 0.34 mmol). The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with EtOAc, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 28 mg of the titled product.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionThe residue is diluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by the flash column chromatography

Sources & evidence

ORD record
ord-7d724e1bda624d11a3b7c4cfa9116518
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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