5'-Chloro-2'-fluoro-N-[(oxan-4-yl)methyl][2,4'-bipyridin]-6-amine → HCID 178511591, compound

HRID 1623351Notes

Reaction equation

HRID 1623351 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:10]=2)=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1>CS(C)=O.O>[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH:30][C:5]2[CH:4]=[C:3]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:16][CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[N:10]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 581271025'-Chloro-2'-fluoro-N-[(oxan-4-yl)methyl][2,4'-bipyridin]-6-amineHCID 178511674HCID 178511674, compound

Product 1

HCID 178511591HCID 178511591, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5′-chloro-2′-fluoro-N-((tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridin-6-amine (500 mg, 1.55 mmol) in DMSO (7 mL) was added trans-1,4-diaminocyclohexane (710 mg, 6.22 mmol). The mixture was stirred at 110° C. for 19 hr. The cooled reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed sequentially with water and brine, dried over sodium sulfate, filtered, and concentrated to give 600 mg of N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-((tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine. LCMS (m/z): 416.1 (MH+), retention time=0.48 min.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b85add6691fc417b82a4b769694eb99b
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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