Cesium carbonate → HCID 58546745, compound

HRID 1850353Notes

Reaction equation

HRID 1850353 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:7]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]3)=[N:8][CH:9]=[CH:10][N:11]=2)[CH2:3]1.Cl[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH3:31])[CH:27]=2)[N:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH3:31][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([N:2]1[CH2:5][CH:4]([C:6]3[C:7]([N:12]4[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]4)=[N:8][CH:9]=[CH:10][N:11]=3)[CH2:3]1)[CH:30]=[CH:29]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 779742-Chloro-6-methylquinolineHCID 67469292HCID 67469292, compound

Product 1

HCID 58546745HCID 58546745, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [1-(3-azetidin-3-yl-pyrazin-2-yl)-piperidin-4-yl]-methanol hydrochloride (284 mg, 1.0 mmol) and 2-chloro-6-methyl-quinoline (purchased from ALDRICH) (177 mg, 1.0 mmol) in DMF (15 mL) was added Cs2CO3 (650 mg, 2.0 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (2×30 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography (EtOAc:Petrol ether=5:1) on silica gel to give (1-{3-[1-(6-methyl-quinolin-2-yl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-4-yl)-methanol (102 mg, 0.26 mmol 26%).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic extracts were washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography (EtOAc:Petrol ether=5:1) on silica gel

Sources & evidence

ORD record
ord-9b52aa63cb45416cadc6129f3d96df0a
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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