Benzene → HCID 86717784, compound

HRID 1468827Notes

Reaction equation

HRID 1468827 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[CH2:11][C@@H:10]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]#[N:19])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:22][S:23]([O-:25])=[O:24].[Na+].C1C=CC=CC=1.CNCCNC>CS(C)=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2]>[CH3:22][S:23]([C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][CH2:8][C@@H:9]2[CH2:11][C@@H:10]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]#[N:19])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 241BenzeneHCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 86717782HCID 86717782, compound

Product 1

HCID 86717784HCID 86717784, compound

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

The product of step C (310 mg, 0.89 mmol), sodium methanesulfinate (109 mg, 1.06 mmol), Cu(OTf)2.C6H6 (89 mg, 0.178 mmol), and MeNHCH2CH2NHMe (0.038 mL, 0.355 mmol) were combined in dimethyl sulfoxide (5 mL) in a glass pressure tube. The solution was purged with nitrogen, sealed, and heated in a 120° C. oil bath overnight. The crude reaction mixture was directly purified by preparative HPLC (C18 reversed phase, gradient elution 10% to 100% MeCN in water with 0.1% formic acid) to yield the desired product.

Workup

  1. customThe solution was purged with nitrogen
  2. customsealed
  3. customThe crude reaction mixture
  4. customwas directly purified by preparative HPLC (C18 reversed phase, gradient elution 10% to 100% MeCN in water with 0.1% formic acid)

Sources & evidence

ORD record
ord-50a0d2824b0041ee86d1adbaee7a103f
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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