Dichloromethane → HCID 86676745, compound

HRID 2406018Notes

Reaction equation

HRID 2406018 reaction equation
[C:1]([NH:8][C:9]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:10]S(C(F)(F)F)(=O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)Cl.[CH2:29]([N:32]1[CH2:37][CH2:36]N[CH2:34][CH2:33]1)[C:30]#[CH:31]>>[C:22]([O:21][C:19](=[O:20])[NH:18][C:9](=[N:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[N:10]1[CH2:36][CH2:37][N:32]([CH2:29][C:30]#[CH:31])[CH2:33][CH2:34]1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 36945701,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidineHCID 146273691-(2-Propynyl)piperazine

Product 1

HCID 86676745HCID 86676745, compoundYield 63%

Procedure

To a solution of N,N′-di-Boc-N″-trifluoromethanesulfonylguanidine (1.72 g, 4.40 mmol) in anhydrous CH2Cl2 (20 mL) Et3N (674 μL, 4.84 mmol) and N-propargyl piperazine (600 mg, 4.84 mmol) are added. The mixture is left reacting at room temperature for 16 h, then the solvent is evaporated. The residue is taken up in EtOAc, and treated with a saturated aqueous NaHCO3 solution and brine. Crude compound is purified by flash chromatography (2:1 EtOAc-petr. et., Rf=0.37) giving compound 4 as a yellow oil (1.01 g, 2.77 mmol) in 63% yield. 1H NMR (CDCl3, 200 MHz) δ 9.61 (br, 1H), 3.44 (m, 4H), 3.16 (d, J=2.6 Hz, 2H), 2.41 (m, 4H), 2.18 (m, 1H), 1.27 (s, 9H) ppm.

Workup

  1. waitThe mixture is left
  2. customthe solvent is evaporated
  3. additiontreated with a saturated aqueous NaHCO3 solution and brine
  4. customCrude compound is purified by flash chromatography (2:1 EtOAc-petr. et., Rf=0.37)

Sources & evidence

ORD record
ord-d7df5ea5d6604cf782458164692f524f
Source dataset
uspto-grants-2014_08
Patent number
US08809338B2

Reaction notes

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