4-Bromo-2-chloropyridine → HCID 178511585, compound

HRID 1623269Notes

Reaction equation

HRID 1623269 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.[C@H:9]1([NH2:16])[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]1>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:15][C@H:12]2[CH2:13][CH2:14][C@H:9]([NH2:16])[CH2:10][CH2:11]2)[CH:3]=1

Participants

4

Reactant 2

HCID 38477704-Bromo-2-chloropyridineHCID 178511674HCID 178511674, compound

Product 1

HCID 178511585HCID 178511585, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-chloropyridine (1500 mg, 7.79 mmol), DMSO (15 ml), and trans-cyclohexane-1,4-diamine (4450 mg, 39.0 mmol) was stirred at 100° C. until the formation of the product, as indicated by LCMS. The reaction mixture was cooled to room temperature, filtered and purified by prep LC, and lyapholized to yield 393 mg of the title compound as a TFA salt. LCMS (m/z): 270.2/272.2 (MH+), retention time=0.31 min.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. custompurified by prep LC

Sources & evidence

ORD record
ord-3c75d3bbd37f46d6a9059dec6587d082
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

Loading…