HCID 67167609, 화합물 → HCID 67167864, 화합물

HRID 874712노트

반응식

HRID 874712 반응식
[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

참가 물질

4

반응물 1

HCID 67167609HCID 67167609, 화합물

생성물 1

HCID 67167864HCID 67167864, 화합물수율 99.6%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-c4ee63cd32524673a97ebcb378662daf
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980926B2

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