Pyridine → HCID 117667737, compound

HRID 712722Notes

Reaction equation

HRID 712722 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]3[NH:12][CH2:13][CH2:14][CH2:15][C:16]=3[CH:17]=2)=[CH:6][N:5]=[CH:4][C:3]=1[CH2:18][O:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26](=[O:28])[CH3:27])[CH2:22][CH2:21]1.N1C=CC=CC=1.[C:35](Cl)(=[O:37])[CH3:36].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[C:35]([N:12]1[C:11]2[N:10]=[CH:9][C:8]([C:7]3[C:2]([Cl:1])=[C:3]([CH2:18][O:19][CH:20]4[CH2:25][CH2:24][N:23]([C:26](=[O:28])[CH3:27])[CH2:22][CH2:21]4)[CH:4]=[N:5][CH:6]=3)=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1)(=[O:37])[CH3:36]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 117667653HCID 117667653, compound

Product 1

HCID 117667737HCID 117667737, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-{4-[4-Chloro-5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-ylmethoxy]-piperidin-1-yl}-ethanone (26 mg, 0.065 mmol) and pyridine (0.016 mL, 0.195 mmol) are dissolved in DCM (1.0 mL) and the mixture is cooled down to 0° C. Acetyl chloride (0.007 mL, 0.097 mmol) is added and the mixture is warmed up to room temperature and stirred for 1 hr. Then saturated NaHCO3 aqueous solution (10 mL) is added along with DCM (30 mL) and water (15 mL). The mixture is stirred for 15 min and the aqueous layer is separated, extracted with DCM (2×10 mL) and EtOAc (2×10 mL). All the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 17 mg of the titled product.

Workup

  1. temperaturethe mixture is warmed up to room temperature
  2. stirringThe mixture is stirred for 15 min
  3. customthe aqueous layer is separated
  4. extractionextracted with DCM (2×10 mL) and EtOAc (2×10 mL)
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-1d41496c24fb43b981d26e1f80f69869
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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