1-Isopropylpiperazine → HCID 71533679, compound

HRID 1504591Notes

Reaction equation

[C:1](=[O:28])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[CH:11][N:10]=2)[CH2:5][CH2:4]1.[CH:29]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)([CH3:31])[CH3:30].CCN(C(C)C)C(C)C>N1C=CC=CC=1>[CH:29]([N:32]1[CH2:37][CH2:36][N:35]([C:1]([O:2][CH:3]2[CH2:4][CH2:5][N:6]([C:9]3[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[CH:11][N:10]=3)[CH2:7][CH2:8]2)=[O:28])[CH2:34][CH2:33]1)([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 30 °C

Procedure

To the solution of 1-(5-carbamoylpyridin-2-yl)-piperidin-4-yl 4-nitrophenyl carbonate (3.0 g, 7.77 mmol) in pyridine (50 ml) was added 1-isopropylpiperazine (1.05 g, 8.16 mmol) and DIPEA (2.01 g, 15.5 mmol). The resulting mixture was stirred at 30° C. for 2 h before it was concentrated to dryness. The residue was further purified by silica gel chromatography (DCM: MeOH=50:1 to 5:1) to afford the title compound as a white solid (1.46 g, 50%). MP: 200.1-203.6° C. [1H NMR (DMSO, 500 MHz): δ 8.61 (d, J=2 Hz, 1H), 7.95 (dd, J=2.5 Hz, 9 Hz, 1H), 7.53 (s, 1H), 7.12 (s, 1H), 6.87 (d, J=9.5 Hz, 1H), 4.83 (m, 1H), 3.90-3.85 (m, 2H), 3.54-3.49 (m, 2H), 3.34 (s, 4H), 2.67-2.64 (m, 1H), 2.38 (m, 4H), 1.89-1.85 (m, 2H), 1.58-1.54 (m, 2H), 0.95 (d, J=6.5 Hz, 6H); LCMS RtA=1.61 min, [M+H]+=376.3].

Workup

concentrationwas concentrated to dryness
customThe residue was further purified by silica gel chromatography (DCM: MeOH=50:1 to 5:1)

Sources & evidence

ORD record: ord-3a0abccd2a3f4ceea753b40ea5111659
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216182B2

Reaction notes

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