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

HRID 1963849Notes

Reaction equation

HRID 1963849 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-17eae2e5b1de4a5381cf6fa6fa03a5cd
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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