Diisopropylethylamine → tert-Butyl 4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazine-1-carboxylate

HRID 416710Notes

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(N(C(C)C)CC)(C)C>C(O)(C)C>[NH2:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[C:3]([N:23]2[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:25][CH2:24]2)[C:2]([Br:1])=[CH:7][N:6]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of 5-bromo-4-chloro-3-nitro-pyridin-2-ylamine (0.126 g, 0.50 mmol) and isopropanol (9 ml) was added 1-BOC-piperazine (0.102 g, 0.55 mmol) followed by diisopropylethylamine (0.10 ml, 0.57 mmol). The reaction mixture was heated at 45° C. for 20 h, then allowed to cool to room temperature, and diluted with isopropanol (3 ml). The precipitate was collected by filtration and washed with isopropanol and diethyl ether. The title compound was thus obtained as a yellow solid (0.112 g, 56%). 1H-NMR (500 MHz, DMSO-d6) 1.42 (s, 9H, C(CH3)3), 2.99 (br s, 4H, piperazine N(CH2)2), 3.45 (br s, 4H, piperazine N(CH2)2), 7.02 (s, 2H, NH2), 8.20 (s, 1H, 6-H); LC (Method B)-MS (ESI, m/z): Rt=5.00 min—402, 404 [(M+H)+, Br isotopic pattern].

Workup

temperatureto cool to room temperature
filtrationThe precipitate was collected by filtration
washwashed with isopropanol and diethyl ether

Sources & evidence

ORD record: ord-4b3a2c6dd4cb4303b8ba627f4686a55b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088761B2

Reaction notes

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