1-(4-Fluorobenzyl)piperazine → 5-Bromo-4-(4-(4-fluorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine

HRID 416891

반응식

HRID 416891 반응식
[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Br:15][C:16]1[C:17](Cl)=[C:18]([N+:23]([O-:25])=[O:24])[C:19]([NH2:22])=[N:20][CH:21]=1>CC(O)C.CCN(C(C)C)C(C)C>[Br:15][C:16]1[C:17]([N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:13]=[CH:14][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:8][CH2:9]2)=[C:18]([N+:23]([O-:25])=[O:24])[C:19]([NH2:22])=[N:20][CH:21]=1

참가 물질

5

반응물 2

HCID 7965631-(4-Fluorobenzyl)piperazineHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amine

생성물 1

HCID 578972785-Bromo-4-(4-(4-fluorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine수율 79.1%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 81531Diisopropylethylamine용매

반응 조건

온도
60 °C

실험 절차

1-(4-Fluorobenzyl)piperazine (0.160 g, 0.81 mmol, 1.05 eq) was suspended in iPrOH (8 mL) and DIPEA (0.72 mL). To this solution, the 5-bromo-4-chloro-3-nitropyridin-2-amine (0.19 g, 0.77 mmol, 1 eq) was added and the reaction mixture was heated and stirred for 17 h at 60° C. The mixture was filtered, washed with iPrOH (3×3 mL), Et2O (2×3 mL) and dried to give the title compound as a bright yellow solid (0.250 g, 75%); 1H-NMR (500 MHz, DMSO-d6): δ 2.43-2.55 (m, 4H, piperazine N(CH2)2), 3.05 (m, 4H, piperazine N(CH2)2), 3.51 (s, 2H, NCH2), 6.96 (br s, 2H, NH2), 7.14 (t, J=9.0 Hz, 2H, ArH), 7.35 (dd, J=8.5, 6.0 Hz, 2H, ArH), 8.15 (s, 1H, pyridine 6-H). LC (Method B)-MS (ESI, m/z): Rt=2.52 min—410/412 [(M+H+), Br isotopic pattern, 100%].

후처리

  1. temperaturethe reaction mixture was heated
  2. filtrationThe mixture was filtered
  3. washwashed with iPrOH (3×3 mL), Et2O (2×3 mL)
  4. customdried

출처 및 근거

ORD 기록
ord-9dadd6b18d07493e8ff356b8ff09cb78
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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