Cesium carbonate → HCID 59652046, compound

HRID 1186859Notes

Reaction equation

HRID 1186859 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[N:12][N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:10](=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.[C:22](=[O:25])([O-])[O-:23].[Cs+].[Cs+]>CN(C=O)C>[C:5]([O:23][C:22]([N:16]1[CH2:17][CH2:18][CH:19]([O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[C:13]([CH3:14])=[N:12][N:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[C:10](=[O:21])[CH:9]=3)=[CH:4][CH:3]=2)[CH2:20][CH2:15]1)=[O:25])([CH3:8])([CH3:6])[CH3:4]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 59651990HCID 59651990, compound

Product 1

HCID 59652046HCID 59652046, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-hydroxyphenyl)-6-methyl-2-pyridin-2-yl-2H-pyridazin-3-one (97.7 g, 28 mmol), t-butyl 4-methanesulfonyloxypiperidine-1-carboxylic acid ester (15 g, 55 mmol) and cesium carbonate (18 g, 55 mmol) in 75 mL of DMF was stirred at 100° C. overnight. The reaction mixture was cooled to rt, filtered through celite, and concentrated. The crude product was diluted with 100 mL of CH2Cl2, washed with 2N NaCO3, water, NaCl solution, then dried over Na2SO4, and concentrated. The product was purified by flash chromatography (5% MeOH in CH2Cl2) and triturated with EtOAc and hexane to give 4-[4-(3-methyl-6-oxo-1-pyridin-2-yl-1,6-dihydropyridazin-4-yl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (6.7 g, 72%): MS m/z 463 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. additionThe crude product was diluted with 100 mL of CH2Cl2
  5. washwashed with 2N NaCO3, water, NaCl solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography (5% MeOH in CH2Cl2)
  9. customtriturated with EtOAc and hexane

Sources & evidence

ORD record
ord-badc231d3e2c4ae1a02d8ae8ad344206
Source dataset
uspto-grants-2014_03
Patent number
US08673916B2

Reaction notes

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