1,2,3,6-Tetrahydropyridine → HCID 20217527, compound

HRID 235862Notes

Reaction equation

HRID 235862 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([NH:12][C:13]([O:15]C3C=CC=CC=3)=O)=[CH:7][CH:8]=2)[N:3]=1.[NH:22]1[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]1>O1CCCC1.C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:9]([CH:8]=[CH:7][C:6]([NH:12][C:13]([N:22]3[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]3)=[O:15])=[N:5]2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 127501,2,3,6-TetrahydropyridineHCID 20217514HCID 20217514, compound

Product 1

HCID 20217527HCID 20217527, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 2-chloro-7-phenoxycarbonylamino-1,8-naphthyridine (15 g) in anhydrous tetrahydrofuran (500 cc), anhydrous acetonitrile (500 cc) and 1,2,5,6-tetrahydropyridine (4.2 g) are added. The mixture is heated under reflux for 45 minutes. The solution is concentrated under reduced pressure (4 kPa) to a volume of 100 cc. After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (3×15 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)-1,2,5,6-tetrahydropyridine-1-carboxamide (10.5 g) is produced, m.p. 173° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 45 minutes
  3. concentrationThe solution is concentrated under reduced pressure (4 kPa) to a volume of 100 cc
  4. customthe crystallised solid is separated by filtration
  5. washwashed with acetonitrile (3×15 cc)
  6. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-1d214080ff9347088309005d98af346b
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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