3-Methylisoquinolin-5-amine → HCID 22807720, compound
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]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.