Pyridine → HCID 86305571, compound

HRID 712595Notes

Reaction equation

HRID 712595 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[NH:13][CH2:12][CH2:11][CH2:10]3)[CH:2]=1.N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[N:13]([C:23](=[O:25])[CH3:24])[CH2:12][CH2:11][CH2:10]3)[CH:2]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 117667315HCID 117667315, compound

Product 1

HCID 86305571HCID 86305571, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

6-Pyridin-3-yl-1,2,3,4-tetrahydro-[1,8]naphthyridine (41 mg, 0.19 mmol) is dissolved in 2 mL of DCM and pyridine (0.19 mL, 2.3 mmol) is added into the solution. Then acetyl chloride (0.08 mL, 1.2 mmol) is added. The mixture is stirred for 0.5 hrs and saturated aqueous NaHCO3 (2 mL) is added along with water (3 mL). The mixture is extracted with EtOAc (3×10 mL) and the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 37 mg of the titled product.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×10 mL)
  2. concentrationconcentrated
  3. customto give the crude product
  4. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-322f6ff0c8534feda80c7511dcc7602d
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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