Diisopropylethylamine → t-Butyl 4-(3-(1-(3-bromophenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate

HRID 2426003

반응식

HRID 2426003 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11]2[CH:16]=[C:15](F)[CH:14]=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[N:21]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(C(C)C)CC)(C)C>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:24]3[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25]3)[CH:14]=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])[CH3:9])[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 58707271N-(1-(3-bromophenyl)ethyl)-5-fluoro-2-nitrobenzenamine

생성물 1

HCID 58707273t-Butyl 4-(3-(1-(3-bromophenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate수율 24.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of N-(1-(3-bromophenyl)ethyl)-5-fluoro-2-nitrobenzenamine (1.25 g, 3.7 mmol), tert-butyl piperazine-1-carboxylate (0.7 g, 3.7 mmol), diisopropylethylamine (1.0 mL, 5.7 mmol) and acetonitrile (20 mL) was heated at reflux for 18 h, cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate; this solution was washed with water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using 10%-15% ethyl acetate in hexanes as eluent to yield the title compounds as a yellow solid (0.45 g, 24%). 1H NMR (400 MHz, CDCl3): δ 8.72 (d, 1 H), 8.10 (d, 1H), 7.51 (s, 1H), 7.40 (m, 1H), 7.24 (m, 2H), 6.17 (dd, 1H), 5.60 (d, 1H), 4.52 (m, 1H), 3.48 (m, 4H), 3.26 (m, 2H), 3.13 (m, 2H), 1.63 (d, 3H), 1.44 (s, 9H). MS (ESI) m/z: Calculated: 504; Observed: 505 (M+H+).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthis solution was washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel using 10%-15% ethyl acetate in hexanes as eluent

출처 및 근거

ORD 기록
ord-35a9035c16fd4913be514fdf979d8d0f
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968538B2

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