3-Aminopyridine → (S)-3-(pyrid-3-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline

HRID 461809Notes

Reaction equation

HRID 461809 reaction equation
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1>N1C=CC=CC=1>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([N:17]=[C:4]2[N:8]3[CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH2:16][C@H:7]3[CH2:6][S:5]2)[CH:19]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Product 1

HCID 22800652(S)-3-(pyrid-3-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolineYield 79.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (36.3 g.) is added, a little at a time, to a solution of 3-aminopyridine (15 g.) in pyridine (1 liter). The suspension gradually passes into solution. After 24 hours at a temperature of about 20° C., the solution is concentrated to dryness under reduced pressure (25 mm. Hg.). The residue is dissolved in a mixture of methylene chloride (250 cc.), 2N sodium hydroxide solution (200 cc.) and water (200 cc.). The organic phase is decanted, dried over magnesium sulphate, filtered and then concentrated under reduced pressure (30 mm. Hg) at 40° C. The residue is recrystallised from acetonitrile (150 cc.) to give (S)-3-(pyrid-3-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (22.4 g.) in the form of white crystals which melt at 111° C.

Workup

  1. concentrationthe solution is concentrated to dryness under reduced pressure (25 mm. Hg.)
  2. dissolutionThe residue is dissolved in a mixture of methylene chloride (250 cc.), 2N sodium hydroxide solution (200 cc.) and water (200 cc.)
  3. customThe organic phase is decanted
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure (30 mm. Hg) at 40° C
  7. customThe residue is recrystallised from acetonitrile (150 cc.)

Sources & evidence

ORD record
ord-c64a5848a61445a4808a88c3fb759e87
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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