1-Methylpiperazine → 2-(5-Acetyl-2-ethylamino-phenylimino)-3-benzyl-5-(4-methylpiperazin-1-ylmethylene)-thiazolidin-4-one

HRID 600826Notes

Reaction equation

HRID 600826 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([C:11]1[CH:12]=[CH:13][C:14]([NH:31][CH2:32][CH3:33])=[C:15]([N:17]=[C:18]2[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21](=[O:30])[CH2:20][S:19]2)[CH:16]=1)(=[O:10])[CH3:9].[CH3:34]OC(OC)N(C)C>C1(C)C=CC=CC=1>[C:8]([C:11]1[CH:12]=[CH:13][C:14]([NH:31][CH2:32][CH3:33])=[C:15]([N:17]=[C:18]2[N:22]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:21](=[O:30])[C:20](=[CH:1][N:2]3[CH2:7][CH2:6][N:5]([CH3:34])[CH2:4][CH2:3]3)[S:19]2)[CH:16]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 78373Dimethylformamide dimethyl acetalHCID 219375832-(5-Acetyl-2-ethylaminophenylimino)-3-benzylthiazolidin-4-one

Product 1

HCID 730725672-(5-Acetyl-2-ethylamino-phenylimino)-3-benzyl-5-(4-methylpiperazin-1-ylmethylene)-thiazolidin-4-oneYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-methylpiperazine (0.22 mL, 2.0 mmol) in N,N-dimethylformamide dimethyl acetal (1.5 mL) was heated at 100° C. After 3 h, the mixture was concentrated under reduced pressure and diluted with toluene (2 cycles), and then concentrated under vacuum. Next an aliquot (80 μL) of the concentrated intermediate was added to a solution of 2-(5-acetyl-2-ethylamino-phenylimino)-3-benzyl-thiazolidin-4-one (60 mg, 0.16 mmol) in toluene (1.0 mL, anhyd). After heating at 120° C. for 1 h, the mixture was cooled, concentrated and chromatographed (silica gel, DCM to 0.2:10:89.8 DEA/MeOH/DCM) to yield the title product (61 mg, 78%) as a yellow solid. 1H-NMR (CDCl3): δ 7.66 (1H, dd), 7.58 (1H, d), 7.55 (1H, s), 7.27-7.42 (5H, m), 6.49 (1H, d), 5.11 (2H, s), 4.12 (1H, br t), 3.45 (4H, br t), 3.03 (2H, m), 2.49 (3K, s), 2.43 (4H, br t), 2.30 (3H, s), 1.02 (3H, t); MS (ESI): 478 (MH+).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additiondiluted with toluene (2 cycles)
  3. concentrationconcentrated under vacuum
  4. temperatureAfter heating at 120° C. for 1 h
  5. temperaturethe mixture was cooled
  6. concentrationconcentrated
  7. customchromatographed (silica gel, DCM to 0.2:10:89.8 DEA/MeOH/DCM)

Sources & evidence

ORD record
ord-5d9386353cae4526865354639a5f238c
Source dataset
uspto-grants-2011_03
Patent number
US07902237B2

Reaction notes

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