1-Methylpiperazine → HCID 135446006, compound

HRID 2369823Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[NH:17][N:16]=2)=[CH:11][CH:10]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:19]=[C:18](/[CH:20]=[CH:21]/[C:22]4[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=4)[NH:17][N:16]=3)=[CH:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

N-Methylpiperazine (50 μL, 0.49 mmol) was added to a suspension of 4-{(E)-2-[3-(4-chlorophenyl)-1H-pyrazol-5-yl]ethenyl}phenol (0.097 g, 0.33 mmol), NaOtBu (0.110 g, 1.14 mmol) and acetato(2′-di-tert-butylphosphino-1,1′-biphenyl-2-yl)palladium (0.015 g, 33 μmol, 10 mol %) in anhydrous toluene (1.5 mL) and heated to 80° C. After 24 hours, the reaction was cooled to room temperature, diluted with methanol and filtered though a celite pad. The filtrate was concentrated in vacuo and the residue purified on reverse phase HPLC using water-acetonitrile gradient (0.1% TFA) to provide the title compound (10 mg, 9% yield) as an off-white solid: 1H NMR (400 MHz, CD3OD): δ 7.71 (m, 2H), 7.40 (m, 2H), 7.20 (d, J=16.4 Hz, 1H), 7.10 (m, 2H), 6.87 (d, J=16.4 Hz, 1H), 6.84 (s, 1H), 6.79 (m, 2H), 3.95 (bd, J=14.4 Hz, 2H), 3.63 (bd, J=11.2 Hz, 2H), 2.28 (m, 2H), 3.10 (bt, J=13.2 Hz, 2H), 2.99 (s, 3H); MS (EI) for C22H24N4O: 361.2 (MH+).

Workup

temperaturethe reaction was cooled to room temperature
filtrationfiltered though a celite pad
concentrationThe filtrate was concentrated in vacuo
customthe residue purified on reverse phase

Sources & evidence

ORD record: ord-d0c099384f444b0f8c6f680eda04d244
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710038B2

Reaction notes

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