(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide → (S)-3-[(3-methylisoquinol-8-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline

HRID 1902544Notes

Reaction equation

HRID 1902544 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]=[CH:20][CH:21]=[C:22]2[C:27]=1[CH:26]=[N:25][C:24]([CH3:28])=[CH:23]2>>[CH3:28][C:24]1[N:25]=[CH:26][C:27]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=[C:4]1[N:8]2[CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:16][C@H:7]2[CH2:6][S:5]1

Participants

3

Reactant 2

HCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodideHCID 205156383-Methylisoquinolin-8-amine

Product 1

HCID 22822245(S)-3-[(3-methylisoquinol-8-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolineYield 53.9%

Procedure

By following the procedure of Example 2, but using (S)-3-methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (8 g) and 8-amino-3-methylisoquinoline (3.5 g) as the starting materials, (S)-3-[(3-methylisoquinol-8-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (4.1 g) is obtained in the form of pale yellow crystals, m.p.=156° C.

Sources & evidence

ORD record
ord-6c70ca65f03f42e0835a2e2f696a97ea
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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