HCID 58127393, compound → HCID 178511603, compound

HRID 1623348Notes

Reaction equation

HRID 1623348 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[N:10]=2)=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH2:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]1>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[N:10]=2)=[CH:4][C:5]([NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 58127393HCID 58127393, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178511603HCID 178511603, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5′-chloro-2′,3,6-trifluoro-2,4′-bipyridine (95 mg, 0.388 mmol) in DMSO (2.5 mL) was added trans-1,4-diaminocyclohexane (177 mg, 1.55 mmol). The mixture was stirred at 90° C. for 2 hr. The cooled reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried (Na2SO4), filtered, and concentrated to give 137 mg of crude trans-N1-(5′-chloro-3,6-difluoro-2,4′-bipyridin-2′-yl)cyclohexane-1,4-diamine which was used without further purification. LCMS (m/z): 339.0 (MH+), retention time=0.54 min

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0f56317a4e1640898d87f5de1bc96812
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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