1-Cyclobutylpiperazine → 1-(6-Oxo-1,6-dihydropyridazin-3-yl)piperidin-4-yl 4-cyclobutylpiperazine-1-carboxylate

HRID 574170Notes

Reaction equation

[C:1](=[O:26])([O:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][C:22](=[O:25])[NH:21][N:20]=2)[CH2:15][CH2:14]1)OC1C=CC([N+]([O-])=O)=CC=1.[CH:27]1([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28]1>C(Cl)Cl>[CH:27]1([N:31]2[CH2:36][CH2:35][N:34]([C:1]([O:12][CH:13]3[CH2:14][CH2:15][N:16]([C:19]4[CH:24]=[CH:23][C:22](=[O:25])[NH:21][N:20]=4)[CH2:17][CH2:18]3)=[O:26])[CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 4-nitrophenyl 1-(6-oxo-1,6-dihydropyridazin-3-yl)piperidin-4-yl carbonate (440 mg, 1.22 mmol) in DCM (20 mL) was added TEA (616 mg, 6.1 mmol) and 1-cyclobutylpiperazine (388 mg, 1.83 mmol). The resulting mixture was stirred at 30° C. for 2 h before it was concentrated to dryness. The title compound was obtained as a white solid after silica gel chromatography (DCM/MeOH=50/1 to 5/1) (410 mg, 93%). [1H NMR (400 MHz, CDCl3) (δ 11.20 (s, 1H), 7.20 (d, J=10 Hz, 1H), 6.87 (d, J=10 Hz, 1H), 4.87˜4.92 (m, 1H), 3.45˜3.50 (m, 6H), 3.16˜3.23 (m, 2H), 2.68˜2.76 (m, 1H), 2.29 (br, 4H), 1.72˜2.07 (m, 10H); LCMS: Rt=1.36 min, m/z 362.3 (M+H)+].

Workup

concentrationwas concentrated to dryness

Sources & evidence

ORD record: ord-8c3cfc1d150d4296a122e314a62a2584
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034874B2

Reaction notes

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