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

HRID 262114Notes

Reaction equation

HRID 262114 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:12][CH2:13][CH3:14])[N:6]=[CH:7]2.[I-].CS[C:18]1[S:19][CH2:20][C@@H:21]2[CH2:30][C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:23][N+:22]=12>>[CH2:12]([C:5]1[N:6]=[CH:7][C:8]2[C:3]([CH:4]=1)=[C:2]([N:1]=[C:18]1[N:22]3[CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[CH2:30][C@H:21]3[CH2:20][S:19]1)[CH:11]=[CH:10][CH:9]=2)[CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodideHCID 203500715-Amino-3-propylisoquinoline

Product 1

HCID 22807721(S)-3-[(3-propylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolineYield 97.3%

Procedure

By following the procedure of Example 3 but using 5-amino-3-propylisoquinoline (0.18 g) and (S)-3-methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (0.35 g) as starting materials, (S)-3-[(3-propylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (0.35 g) is obtained in a crude form, which is purified by chromatography on a column (diameter of the column: 0.7 cm) containing silica (6 g) by eluting with methylene chloride and collecting the eluate in 20 cc fractions.

Sources & evidence

ORD record
ord-61b256e79ec5408b8ad59845a675c70a
Source dataset
uspto-grants-1979_05
Patent number
US04153698

Reaction notes

Loading…