Methyl p-toluenesulfonate → 2-(5-acetyl-2-ethylamino-phenylimino)-3-benzyl-5-({N-[4-(2-methoxy-ethoxy)-phenyl]-methylamino}-methylene)-thiazolidin-4-one

HRID 600829Notes

Reaction equation

HRID 600829 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:14][N:15]([CH3:27])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:18][CH:17]=2)[S:10][C:9]1=S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(OC)(=O)=O)=CC=1.[NH2:41][C:42]1[CH:43]=[C:44]([C:51](=[O:53])[CH3:52])[CH:45]=[CH:46][C:47]=1[NH:48][CH2:49][CH3:50]>CN(C=O)C>[C:51]([C:44]1[CH:45]=[CH:46][C:47]([NH:48][CH2:49][CH3:50])=[C:42]([N:41]=[C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:12](=[O:13])[C:11](=[CH:14][N:15]([CH3:27])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:18][CH:17]=3)[S:10]2)[CH:43]=1)(=[O:53])[CH3:52]

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 219373693'-Amino-4'-(ethylamino)acetophenoneHCID 866204243-benzyl-5-({N-[4-(2-methoxy-ethoxy)-phenyl]-methylamino}-methylene)-2-thioxothiazolidin-4-one

Product 1

HCID 729846032-(5-acetyl-2-ethylamino-phenylimino)-3-benzyl-5-({N-[4-(2-methoxy-ethoxy)-phenyl]-methylamino}-methylene)-thiazolidin-4-oneYield 8.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-benzyl-5-({N-[4-(2-methoxy-ethoxy)-phenyl]-methylamino}-methylene)-2-thioxothiazolidin-4-one (60 mg, 0.14 mmol) and methyl p-toluenesulfonate (54 mg, 0.29 mmol) in DMF (1.0 mL, anhyd) was heated at 130° C. After 2 h the reaction mixture was allowed to cool to ambient temperature, charged with 3′-amino-4′-ethylamino-acetophenone (50 mg, 0.28 mmol) and TEA (70 μL, 0.72 mmol), and then heated at 65° C. After 20 h the reaction mixture was cooled and chromatographed (HPLC-MS conditions) to yield the title product (7 mg) as a yellow solid. 1H-NMR (CDCl3): δ 7.82 (1H, s), 7.61 (1H, dd), 7.48 (1H, d), 7.27-7.40 (5H, m), 7.08 (2H, m), 6.90 (2H, m), 6.44 (1H, d), 5.09 (2H, s), 4.20 (1H, br s), 4.07 (2H, m), 3.73 (2H, m), 3.46 (3H, s), 3.44 (3H, s), 3.00 (2H, m), 2.43 (3H, s), 1.00 (3H, t); MS (ESI): 559 (MH+).

Workup

  1. temperatureto cool to ambient temperature
  2. temperatureheated at 65° C
  3. temperatureAfter 20 h the reaction mixture was cooled
  4. customchromatographed (HPLC-MS conditions)

Sources & evidence

ORD record
ord-a37c0270ad2149b0952baa9757603995
Source dataset
uspto-grants-2011_03
Patent number
US07902237B2

Reaction notes

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