HCID 28548490, compound → HCID 58548679, compound

HRID 1846782Notes

Reaction equation

HRID 1846782 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.F[C:17]1[C:22]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:21][CH:20]=[CH:19][N:18]=1>CS(C)=O.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][CH:12]([O:15][C:17]3[C:22]([CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 28548490HCID 28548490, compoundHCID 593271552-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine

Product 1

HCID 58548679HCID 58548679, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

4-(5-methyl-pyridin-2-ylamino)-cyclohexanol (50 mg) was added to a solution of 2-fluoro-3-(tetrahydro-pyran-4-yl)-pyridine, as prepared in preparation 1a, (50 mg) in DMSO (15 mL) and the reaction mixture was stirred until TLC analysis confirmed the absence of starting materials. Then the mixture was diluted with water (10 mL), and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with water (5 mL) and brine (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by column chromatography (EtOAc:Petrol ether=1:1) to provide (5-methyl-pyridin-2-yl)-{4-[3-(tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclohexyl}-amine (0.03 g, yield 60%) as a solid. [M+1] 368. IC50 (uM): 0.057.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic extracts were washed with water (5 mL) and brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by column chromatography (EtOAc:Petrol ether=1:1)

Sources & evidence

ORD record
ord-6422531d34464d71b4b024a9e6660608
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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