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

HRID 579323노트

반응식

HRID 579323 반응식
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

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 30925302,5-Dibromo-1,3,4-thiadiazole

생성물 1

HCID 66545097tert-Butyl 4-(5-bromo-1,3,4-thiadiazol-2-yl)piperazine-1-carboxylate수율 77.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3c45f90032db43f989c41b1751e5e747
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040712B2

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