HCID 67167609, compound → HCID 67167864, compound

HRID 874712Notes

Reaction equation

HRID 874712 reaction equation
[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

Participants

4

Reactant 1

HCID 67167609HCID 67167609, compound

Product 1

HCID 67167864HCID 67167864, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-c4ee63cd32524673a97ebcb378662daf
Source dataset
uspto-grants-2015_03
Patent number
US08980926B2

Reaction notes

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