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

HRID 1527740ノート

反応式

HRID 1527740 の反応式
[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

参加物

5

反応物 2

HCID 947NitrogenHCID 90410701HCID 90410701、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bb6fad8bf57d4e8aabec63bbcf468442
出典データセット
uspto-grants-2015_07
特許番号
US09089569B2

反応ノート

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