3-Methylisoquinolin-5-amine → HCID 22807720, compound

HRID 262107Notes

Reaction equation

HRID 262107 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]([CH3:28])[N:22]=[CH:23]2>N1C=CC=CC=1>[CH3:28][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 122120553-Methylisoquinolin-5-amineHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Product 1

HCID 22807720HCID 22807720, compoundYield 84.6%

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 to a solution of 5-amino-3-methylisoquinoline (15.9 g) in pyridine (200 cc). The suspension obtained gradually goes into solution. After 24 hours at a temperature of about 20° C., the mixture is concentrated to dryness under reduced pressure (25 mm Hg) at 50° C. The residue is dissolved in a mixture of methylene chloride (600 cc) and N aqueous sodium hydroxide solution (400 cc). The organic phase is decanted, washed with water (200 cc), dried over magnesium sulphate, filtered and the filtrate is then concentrated to dryness under reduced pressure (40 mm Hg) at 40° C. The residue obtained is recrystallised from acetonitrile (500 cc). (S)-3-[(3-Methylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo-[3,4-b]isoquinoline (29.2 g), which melts at 181° C., is thus obtained.

Workup

  1. customThe suspension obtained gradually
  2. concentrationthe mixture is concentrated to dryness under reduced pressure (25 mm Hg) at 50° C
  3. dissolutionThe residue is dissolved in a mixture of methylene chloride (600 cc) and N aqueous sodium hydroxide solution (400 cc)
  4. customThe organic phase is decanted
  5. washwashed with water (200 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationthe filtrate is then concentrated to dryness under reduced pressure (40 mm Hg) at 40° C
  9. customThe residue obtained
  10. customis recrystallised from acetonitrile (500 cc)

Sources & evidence

ORD record
ord-2cd115a9a5ec4420b55be3509b1b83c7
Source dataset
uspto-grants-1979_05
Patent number
US04153698

Reaction notes

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