2-Chloropyridine → HCID 59374083, compound

HRID 473686Notes

Reaction equation

HRID 473686 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:2]1.Cl[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1>C(=O)(O)[O-].[Na+]>[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH:18][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:2]1

Participants

4

Reactant 2

HCID 79772-ChloropyridineHCID 59351239HCID 59351239, compound

Product 1

HCID 59374083HCID 59374083, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

4-(3-(Tetrahydro-2H-pyran-3-yl)pyrazin-2-yloxy)aniline (0.10 g, 0.38 mmol) and 2-chloropyridine (0.072 mL, 0.76 mmol) were mixed together neat in a microwave tube. The tube was sealed and stirred at 120° C. for 45 min before being warmed to 160° C. and stirred for 2 h. The reaction mixture was cooled to room temperature, diluted with sat. sodium bicarbonate, and extracted with EtOAc (2×). The combined organic layers were washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography to give N-(4-(3-(tetrahydro-2H-pyran-3-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 349.1 (M+1). IC50 (uM) 0.021.

Workup

  1. customThe tube was sealed
  2. temperaturebefore being warmed to 160° C.
  3. stirringstirred for 2 h
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionextracted with EtOAc (2×)
  6. washThe combined organic layers were washed with sat. sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d65874ec24d0420f97b1d5e99b0d4e68
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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