Pyridine → HCID 86738680, compound

HRID 1902548Notes

Reaction equation

HRID 1902548 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.N[C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[C:21]([C:28]([O:30][CH3:31])=[O:29])[N:22]=[CH:23]2.[N:32]1C=CC=CC=1>>[CH3:31][O:30][C:28]([C:21]1[N:22]=[CH:23][C:24]2[C:19]([CH:20]=1)=[C:18]([C@H:4]1[N:8]3[CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH2:16][CH:7]3[C:6](=[NH:32])[S:5]1)[CH:27]=[CH:26][CH:25]=2)=[O:29]

Participants

4

Reactant 3

HCID 1049PyridineHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodideHCID 22032628Methyl 5-aminoisoquinoline-3-carboxylate

Product 1

HCID 86738680HCID 86738680, compound

Conditions

Temperature
20 °C

Procedure

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo-[3,4-b]isoquinolinium iodide (22.4 g) is added to a solution of 5-amino-3-methoxycarbonylisoquinoline (13 g) in pyridine (400 cc). The suspension gradually changes to a solution. After stirring for 3 days at a temperature of the order of 20° C., the mixture is concentrated to dryness under reduced pressure (20 m Hg; 2.7 kPa) at 60° C. The residue is dissolved in methylene chloride (500 cc) and the solution is washed with a N aqueous sodium hydroxide (3×300 cc) and then with water. The solution is dried over sodium 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 recrystallised from acetonitrile (500 cc). After filtration, washing with diisopropyl ether and drying, (S)-3-[(3-methoxycarbonylisoquinol-5-yl)]-imino-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline (12.8 g) is obtained, as a pale yellow solid, m.p.=200° C.

Workup

  1. concentrationthe mixture is concentrated to dryness under reduced pressure (20 m Hg; 2.7 kPa) at 60° C
  2. dissolutionThe residue is dissolved in methylene chloride (500 cc)
  3. washthe solution is washed with a N aqueous sodium hydroxide (3×300 cc)
  4. dry with materialThe solution is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  7. customThe residue is recrystallised from acetonitrile (500 cc)
  8. filtrationAfter filtration
  9. washwashing with diisopropyl ether
  10. customdrying

Sources & evidence

ORD record
ord-d9b17c24cb2a498eb3fe2d982a19b350
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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