Diisopropylethylamine → HCID 90410701, 화합물

HRID 1527739노트

반응식

HRID 1527739 반응식
F[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[O:5][CH2:6][C:7]1[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=1.[F:19][C:20]1[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=1[CH2:31][NH2:32].CCN(C(C)C)C(C)C>C(#N)C>[F:19][C:20]1[CH:25]=[C:24]([O:26][C:27]([F:28])([F:29])[F:30])[CH:23]=[CH:22][C:21]=1[CH2:31][NH:32][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=2)[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 665234822-Fluoro-4-(trifluoromethoxy)benzenemethanamineHCID 828819703-((3-Fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole

생성물 1

HCID 90410701HCID 90410701, 화합물수율 94.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 3-((3-fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole (70.0 g, 0.28 mol), (2-fluoro-4-(trifluoromethoxy)phenyl)methanamine (58.3 g, 0.28 mol), DIPEA (63.1 mL, 0.36 mol) and acetonitrile (350 mL) was stirred at 80° Celsius for 16 h. The reaction was cooled to RT, concentrated to dryness, and the resulting residue was recrystallized from ethanol (350 mL) and H2O (350 mL). The solid was collected by filtration and rinsed with a mixture of H2O/ethanol (3:1, 200 mL) followed by hexanes (2×300 mL) yielding the title compound as a yellow solid (116.3 g, 94.7%). MS (ESI): mass calcd. for C19H16F4N4O4, 440.1; m/z found, 441.0 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 8.68-8.52 (m, 1H), 8.20-8.14 (d, J=9.5, 1H), 7.39-7.34 (m, 1H), 7.34-7.31 (d, J=2.2, 1H), 7.06-6.97 (d, J=9.8, 2H), 6.42-6.33 (dd, J=9.5, 2.5, 1H), 6.33-6.24 (m, 2H), 5.09-5.01 (s, 2H), 4.60-4.52 (d, J=5.9, 2H), 3.93-3.85 (s, 3H).

후처리

  1. concentrationconcentrated to dryness
  2. customthe resulting residue was recrystallized from ethanol (350 mL) and H2O (350 mL)
  3. filtrationThe solid was collected by filtration
  4. washrinsed with a mixture of H2O/ethanol (3:1, 200 mL)

출처 및 근거

ORD 기록
ord-d6a48594d09547149cb62443e66cf078
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09089569B2

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