1-Methyl-6-sulfanyl-3,4-dihydroquinoline-2-thione → (2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-thioxo-1,2,3,4-tetrahydroquinolin-6-ylthio)thiazol-5-yl]tetrahydropyran

HRID 2260631Notes

Reaction equation

HRID 2260631 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[S:13])[CH2:6][CH2:5]2.Cl[C:15]1[S:16][C:17]([C@@:20]2([OH:27])[CH2:25][CH2:24][O:23][C@@H:22]([CH3:26])[CH2:21]2)=[CH:18][N:19]=1>>[OH:27][C@:20]1([C:17]2[S:16][C:15]([S:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]([CH3:12])[C:7](=[S:13])[CH2:6][CH2:5]4)=[N:19][CH:18]=2)[CH2:25][CH2:24][O:23][C@@H:22]([CH3:26])[CH2:21]1

Participants

3

Reactant 2

HCID 224137821-Methyl-6-sulfanyl-3,4-dihydroquinoline-2-thioneHCID 54155591(2S,4R)-4-(2-chlorothiazol-5-yl)-4-hydroxy-2-methyltetrahydropyran

Product 1

HCID 54293520(2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-thioxo-1,2,3,4-tetrahydroquinolin-6-ylthio)thiazol-5-yl]tetrahydropyranYield 45%

Procedure

Using an analogous procedure to that described in Example 3, 6-mercapto-1-methyl-2-thioxo-1,2,3,4-tetrahydroquinoline was reacted with (2S,4R)-4-(2-chlorothiazol-5-yl)-4-hydroxy-2-methyltetrahydropyran to give (2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-thioxo-1,2,3,4-tetrahydroquinolin-6-ylthio)thiazol-5-yl]tetrahydropyran as a foam (0.365 g, 45%);

Sources & evidence

ORD record
ord-9b935e116b954c7da1a8f3bb4aed5462
Source dataset
uspto-grants-1995_12
Patent number
US05478842

Reaction notes

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