1,2,3,4-Tetrahydroisoquinoline → 3-Methyl-4-[3-(1,2,3,4-tetrahydroisoquinolin-1-yl)propylthio]-2-[(4-pyridinylthio)methyl]pyridine

HRID 1275564Notes

Reaction equation

HRID 1275564 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][S:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[C:7]=1[CH3:20].[CH2:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][NH:22]1.C(O)(C)C.C(OC(C)C)(C)C>>[CH3:20][C:7]1[C:8]([CH2:12][S:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[N:9][CH:10]=[CH:11][C:6]=1[S:5][CH2:4][CH2:3][CH2:2][CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][NH:22]1

Participants

4

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 21202047Isopropyl alcohol isopropyl etherHCID 221173024-(3-Chloropropylthio)-3-methyl-2-[(4-pyridinylthio)methyl]pyridine

Product 1

HCID 221173363-Methyl-4-[3-(1,2,3,4-tetrahydroisoquinolin-1-yl)propylthio]-2-[(4-pyridinylthio)methyl]pyridineYield 36%

Procedure

According to the procedure indicated in Example 7, reaction of 4-(3-chloropropylthio)-3-methyl-2-[(4-pyridinylthio)methyl]pyridine with 1,2,3,4-tetrahydroisoquinoline, chromatography on silica gel and subsequent crystallization from isopropanol/diisopropyl ether gives the title compound; m.p. 190-192° C.; yield 36% of theory.

Sources & evidence

ORD record
ord-2622ae1696244e45ac47aaef6f3ae413
Source dataset
uspto-grants-2000_12
Patent number
US06162809

Reaction notes

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