HCID 67167609、化合物 → HCID 67167864、化合物

HRID 874712ノート

反応式

HRID 874712 の反応式
[F:1][C:2]([F:28])([F:27])[C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([C:14]3[CH:20]=[C:19]([C:21]#[C:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:18]=[CH:17][C:15]=3[NH2:16])=[O:13])=[CH:8][CH:7]=2)[NH:5][NH:4]1>C(OCC)C.[O-2].[Mn+4].[O-2]>[F:28][C:2]([F:1])([F:27])[C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([C:14]3[CH:20]=[C:19]([C:21]#[C:22][Si:23]([CH3:25])([CH3:24])[CH3:26])[CH:18]=[CH:17][C:15]=3[NH2:16])=[O:13])=[CH:8][CH:7]=2)[N:5]=[N:4]1

参加物

4

反応物 1

HCID 67167609HCID 67167609、化合物

生成物 1

HCID 67167864HCID 67167864、化合物収率 99.6%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 3283Diethyl Ether溶媒

実験手順

2-({4-[3-(trifluoromethyl)diaziridin-3-yl]phenyl}carbonyl)-4-[2-(trimethylsilyl)ethynyl]aniline (66 mg, 0.16 mmol, 1 eq.) was dissolved in diethyl ether (10 mL) and manganese(IV) oxide (300 mg, 3.4 mmol, 21 eq.) was added to the solution. The reaction was stirred at room temperature for 30 minutes and then filtered through Celite with DCM to remove the manganese(IV) oxide. The solvent was evaporated, and the residue was purified on silica column (hexanes/ethyl acetate, 9:1→2:1), resulting in 64 mg (97%) of the title compound as a yellow-orange solid. 1H NMR (500 MHz, CDCl3) δ 7.63 (d, J=8.4, 2H, Ar—H), 7.46 (d, J=1.7, 1H, Ar—H), 7.37 (dd, J=1.8, 8.6, 1H, Ar—H), 7.28 (d, J=8.2, 2H, Ar—H), 6.64 (d, J=8.6, 1H, Ar—H), 6.30 (s, 2H, NH2), 0.18 (s, 9H, Si(CH3)3). 13C NMR (126 MHz, CDCl3) δ 197.20 (CO), 151.24 (C—Ar), 140.72 (C—Ar), 138.19 (C—Ar), 137.94 (C—Ar), 132.27 (C—Ar), 129.59 (C—Ar), 126.48 (q, C—Ar, J=1.19), 122.13 (q, J=274.80, CF3), 117.35 (C—Ar), 117.10 (C—Ar), 110.28 (C—Ar), 104.86 (CSi(CH3)3), 92.21 (CCSi(CH3)3), 28.62 (q, J=40.69, CN2), 0.22 (Si(CH3)3). Exact Mass, 401.12. 399.7011 [M−H]−, 401.7108 [M+H]+.

後処理

  1. filtrationfiltered through Celite with DCM
  2. customto remove the manganese(IV) oxide
  3. customThe solvent was evaporated
  4. customthe residue was purified on silica column (hexanes/ethyl acetate, 9:1→2:1)

出典と根拠

ORDレコード
ord-c4ee63cd32524673a97ebcb378662daf
出典データセット
uspto-grants-2015_03
特許番号
US08980926B2

反応ノート

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