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

HRID 461815Notes

Reaction equation

HRID 461815 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[I-].CS[C:15]1[S:16][CH2:17][C@@H:18]2[CH2:27][C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:20][N+:19]=12>N1C=CC=CC=1>[CH:7]1[C:8]2[C:3](=[C:2]([N:1]=[C:15]3[N:19]4[CH2:20][C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=5[CH2:27][C@H:18]4[CH2:17][S:16]3)[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 707665-AminoisoquinolineHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Product 1

HCID 22800655(S)-3-(isoquinol-5-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b] isoquinolineYield 78.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

5-Aminoisoquinoline (10.8 g.) is added to a solution of (S)-3-methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (18.2 g.) in pyridine (500 cc.). After 5 hours at a temperature of about 20° C., solution is complete and the reaction is allowed to continue for 10 hours. The solution is concentrated to dryness under reduced pressure (25 mm.Hg) at 60° C. The residue is dissolved in a mixture consisting of N sodium hydroxide solution (250 cc.) and methylene chloride (250 cc.). The organic phase is decanted, washed with water (2 × 100 cc.), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (50 mm.Hg) at 40° C. Isopropanol (150 cc.) is added to the residue obtained; the mixture is brought to the boil and is filtered hot. After cooling to 5° C., the crystals formed and filtered off and washed with isopropanol (3 × 10 cc.). After drying at 60° C., under reduced pressure (0.1 mm.Hg), (S)-3-(isoquinol-5-ylimino)-1,5,10,10a-tetrahydrothiazolo[3,4-b] isoquinoline (13.0 g.) is obtained in the form of white crystals melting at 164° C.

Workup

  1. waitto continue for 10 hours
  2. concentrationThe solution is concentrated to dryness under reduced pressure (25 mm.Hg) at 60° C
  3. dissolutionThe residue is dissolved in a mixture
  4. customThe organic phase is decanted
  5. washwashed with water (2 × 100 cc.)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (50 mm.Hg) at 40° C
  9. additionIsopropanol (150 cc.) is added to the residue
  10. customobtained
  11. filtrationis filtered hot
  12. customthe crystals formed
  13. filtrationfiltered off
  14. washwashed with isopropanol (3 × 10 cc.)
  15. customAfter drying at 60° C., under reduced pressure (0.1 mm.Hg)

Sources & evidence

ORD record
ord-5d18cab1682140f4ae04fc437910f843
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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