Nitrogen → N1-(2-Fluoro-4-(trifluoromethoxy)benzyl)-5-((1-methyl-1H-pyrazol-3-yl)methoxy)benzene-1,2-diamine

HRID 1527740노트

반응식

HRID 1527740 반응식
[F:1][C:2]1[CH:26]=[C:25]([O:27][C:28]([F:31])([F:30])[F:29])[CH:24]=[CH:23][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=2)[CH:9]=[CH:8][C:7]=1[N+:20]([O-])=O.N#N>[Pt].C(OCC)(=O)C>[F:1][C:2]1[CH:26]=[C:25]([O:27][C:28]([F:30])([F:29])[F:31])[CH:24]=[CH:23][C:3]=1[CH2:4][NH:5][C:6]1[C:7]([NH2:20])=[CH:8][CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=2)[CH:11]=1

참가 물질

5

반응물 2

HCID 947NitrogenHCID 90410701HCID 90410701, 화합물

생성물 1

HCID 131732437N1-(2-Fluoro-4-(trifluoromethoxy)benzyl)-5-((1-methyl-1H-pyrazol-3-yl)methoxy)benzene-1,2-diamine수율 100.9%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 8857Ethyl Acetate용매

실험 절차

In a high pressure reactor a solution of N-(2-fluoro-4-(trifluoromethoxy)benzyl)-5-((1-methyl-1H-pyrazol-3-yl)methoxy)-2-nitroaniline (80.0 g, 0.18 mol), 5% Pt/C (50% H2O, Johnson Matthey B102022-5) (7.1 g, 0.91 mmol) and ethyl acetate (800 mL) was filled twice with N2 (60 psi) then twice with H2 (60 psi). The flask was then filled with H2 (60 psi) and let stir at RT 15 h. The reaction mixture was filtered (zapcap brand filter), the solid was rinsed with EtOAc (2×200 mL). The filtrate was concentrated to dryness to afford the title compound as a brown oil (74.5 g, 99.5%). This material was used without further purification. MS (ESI): mass calcd. for C19H18F4N4O2, 410.1; m/z found, 411.1 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 7.42-7.35 (m, 1H), 7.33-7.29 (d, J=2.2, 1H), 7.01-6.94 (d, J=9.2, 1H), 6.71-6.66 (d, J=8.3, 1H), 6.37-6.31 (dd, J=8.3, 2.7, 1H), 6.31-6.26 (m, 1H), 4.98-4.94 (s, 1H), 4.41-4.33 (s, 1H), 3.93-3.85 (s, 2H), 3.35-2.72 (s, 1H).

후처리

  1. additionThe flask was then filled with H2 (60 psi)
  2. filtrationThe reaction mixture was filtered
  3. filtration(zapcap brand filter)
  4. washthe solid was rinsed with EtOAc (2×200 mL)
  5. concentrationThe filtrate was concentrated to dryness

출처 및 근거

ORD 기록
ord-bb6fad8bf57d4e8aabec63bbcf468442
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09089569B2

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