Diisopropylethylamine → 5-Bromo-3-nitro-4-(4-(1-phenylethyl)piperazin-1-yl)pyridin-2-amine

HRID 416798Notes

Reaction equation

[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([Br:12])=[CH:4][N:3]=1.[C:13]1([CH:19]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[Br:12][C:5]1[C:6]([N:24]2[CH2:25][CH2:26][N:21]([CH:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:20])[CH2:22][CH2:23]2)=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 2-amino-5-bromo-4-chloro-3-nitropyridine (0.252 g, 1.00 mmol) and isopropanol (18 ml) was added 1-(1-phenylethyl)piperazine (0.209 g, 1.10 mmol) followed by diisopropylethylamine (0.20 ml, 1.15 mmol). The reaction mixture was stirred at 45° C. for 20 h, then allowed to cool to room temperature and diluted with isopropanol (10 ml). The resulting precipitate was collected by filtration, washed with isopropanol (3×5 ml), diethyl ether (3×5 ml), and dried. The title compound was obtained as a yellow solid (0.300 g, 74%). 1H-NMR (500 MHz, DMSO-d6) 1.30 (d, J=6.7 Hz, 3H, CHCH3), 2.42 (m, 2H) and 2.54 (m, 2H) (piperazine N(CH2)2), 3.03 (br s, 4H, piperazine N(CH2)2), 3.45 (q, J=6.7 Hz, 1H, CHCH3), 6.95 (s, 2H, NH2), 7.23 (m, 1H) and 7.32 (m, 4H) (PhH), 8.13 (s, 1H, pyridine 6-H);

Workup

temperatureto cool to room temperature
filtrationThe resulting precipitate was collected by filtration
washwashed with isopropanol (3×5 ml), diethyl ether (3×5 ml)
customdried

Sources & evidence

ORD record: ord-5f8498332b2c4ef2a53f5ac5ab626a17
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088761B2

Reaction notes

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