5-Amino-3-methoxymethylisoquinoline → (S)-3-[(3-Methoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline

HRID 1577084Notes

Reaction equation

HRID 1577084 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:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[C:21]([CH2:28][O:29][CH3:30])[N:22]=[CH:23]2>N1C=CC=CC=1>[CH3:30][O:29][CH2:28][C:21]1[N:22]=[CH:23][C:24]2[C:19]([CH:20]=1)=[C:18]([N:17]=[C:4]1[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]1)[CH:27]=[CH:26][CH:25]=2

Participants

4

Reactant 2

HCID 128748525-Amino-3-methoxymethylisoquinolineHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Product 1

HCID 22817329(S)-3-[(3-Methoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolineYield 84.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (13.0 g) is added to a solution of 5-amino-3-methoxymethylisoquinoline (6.8 g) in pyridine (200 cc). After 18 hours at a temperature of about 20° C., the mixture is concentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa). The residue is dissolved in a mixture of 4 N sodium hydroxide solution (100 cc) and methylene chloride (200 cc). The organic phase is decanted, washed with water (100 cc), dried over magnesium sulphate and filtered, and the filtrate is then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue is crystallized by trituration with diisopropyl ether (50 cc) and then recrystallised from ethanol (200 cc). (S)-3-[(3-Methoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (11.3 g) is thus obtained in the form of light beige crystals melting at 134° C.

Workup

  1. concentrationthe mixture is concentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa)
  2. dissolutionThe residue is dissolved in a mixture of 4 N sodium hydroxide solution (100 cc) and methylene chloride (200 cc)
  3. customThe organic phase is decanted
  4. washwashed with water (100 cc)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  8. customThe residue is crystallized by trituration with diisopropyl ether (50 cc)
  9. customrecrystallised from ethanol (200 cc)

Sources & evidence

ORD record
ord-229b4b4e61524d7f9cf02d4856beb99d
Source dataset
uspto-grants-1981_09
Patent number
US04287197

Reaction notes

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