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

HRID 579323Notes

Reaction equation

CCN(C(C)C)C(C)C.[Br:10][C:11]1[S:12][C:13](Br)=[N:14][N:15]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>O1CCOCC1>[Br:10][C:11]1[S:12][C:13]([N:20]2[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)=[N:14][N:15]=1

Participants

Conditions

Temperature: 120 °C

Procedure

DIPEA (430 μL, 2.460 mmol) was added to a stirred solution of 2,5-dibromo-1,3,4-thiadiazole (300 mg, 1.230 mmol) and tert-butyl piperazine-1-carboxylate (275 mg, 1.476 mmol) in dioxane (4 mL). The reaction mixture was heated at 120° C. for 2 hours. The reaction mixture was cooled to room temperature, filtered under vacuum, rinsed with dioxane, and the filtrate was concentrated in vacuo to afford the crude product as an orange oily residue. The crude material was purified by preparative HPLC under neutral conditions (ammonium formate modified) to afford the title compound as a yellow solid (331 mg, 77% yield). LC-MS: Rt 1.18 min; MS m/z 351.1 [M+2]+ [Method A]. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.38-3.55 (m, 8H), 1.41 (s, 9H).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered under vacuum
washrinsed with dioxane
concentrationthe filtrate was concentrated in vacuo
customto afford the crude product as an orange oily residue
customThe crude material was purified by preparative HPLC under neutral conditions (ammonium formate modified)

Sources & evidence

ORD record: ord-3c45f90032db43f989c41b1751e5e747
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040712B2

Reaction notes

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