Potassium Carbonate → HCID 178482266, compound

HRID 1963936Notes

Reaction equation

HRID 1963936 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][CH2:23][CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[N:16]=3)[C:12]([Cl:30])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[C:31](=O)([O-])[O-].[K+].[K+].CC1C=CC(S(OC[CH:49]2[CH2:52][CH2:51][O:50]2)(=O)=O)=CC=1>CS(C)=O.O>[Cl:30][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][CH2:23][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:16]=2)=[CH:14][C:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([N:1]([CH:49]3[CH2:52][CH2:51][O:50]3)[CH3:31])[CH2:3][CH2:4]2)=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13927594Oxetan-2-ylmethyl 4-methylbenzenesulfonateHCID 178511593HCID 178511593, compound

Product 1

HCID 178482266HCID 178482266, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
83 °C

Procedure

To a stirred solution of N2′-(trans-4-aminocyclohexyl)-5′-chloro-5-fluoro-N6-((tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine (90 mg, 0.207 mmol)) in DMSO (1.0 ml) was add potassium carbonate (71.7 mg, 0.518 mmol), followed by follow oxetan-2-yl-methyl 4-methylbenzenesulfonate (151 mg, 0.622 mmol). The mixture was heated at 83° C. for 2 h. The mixture was allowed to cool to ambient temperature, then diluted with water and then extracted with EtOAc (×3). The organics were combined then washed with water (×2), saturated brine (×2), then dried (Na2SO4), filtered and evaporated under reduced pressure. The resulting residue was purified by reverse phase prep HPLC and lyophilized to yield titled compound. LCMS (m/z): 504.4/506.5 (MH+) retention time=0.60 min as a TFA salt.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with EtOAc (×3)
  3. washThe organics were combined then washed with water (×2), saturated brine (×2)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe resulting residue was purified by reverse phase prep HPLC

Sources & evidence

ORD record
ord-50d3e7a8746d412190e6ba6bc0729e49
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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