Cysteamine → 1-Hexyl-3-(2-thiazolidinyl)-4-methoxy-6-methyl-2(1H)-quinolinone

HRID 36047Notes

Reaction equation

HRID 36047 reaction equation
[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH:20]=O)[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:23][CH2:24][CH2:25][SH:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH2:1]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([O:18][CH3:19])=[C:9]([CH:20]2[NH:23][CH2:24][CH2:25][S:26]2)[C:8]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6058CysteamineHCID 6101p-Toluenesulfonic acidHCID 152333661-hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone

Product 1

HCID 152333381-Hexyl-3-(2-thiazolidinyl)-4-methoxy-6-methyl-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 -hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone (Step (2) of Example 1, 1 g) and 2-aminoethanethiol (0.26 g) in methylene chloride (20 ml) containing p-toluenesulfonic acid (0.1 g) was stirred for 3hrs. The mixture was washed with aqueous sodium bicarbonate, dried, evaporated and then crystallized from ether-hexane to give 1-Hexyl-3-(2-thiazolidinyl)-4-methoxy-6-methyl-2(1H)-quinolinone. That the expected product was obtained was confirmed by the spectral data: MS: m/e 360 (M+); NMR (CDCl3): δ3.17 (m, 2H, CH2S), 3.86 (m, 2H, CH2N), 6.0 (d, 1H, S-CH-N).

Workup

  1. washThe mixture was washed with aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. customcrystallized from ether-hexane

Sources & evidence

ORD record
ord-bb6a6eecb42f44aab06bddffdb2f7544
Source dataset
uspto-grants-1995_05
Patent number
US05412104

Reaction notes

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