Sodium Bicarbonate → 1-Butyl-3-chloro-4-[4-(4-oxo-cyclohexyl)-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl]-1H-pyridin-2-one

HRID 2364951Notes

Reaction equation

HRID 2364951 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:25]=[CH:24][C:12]3[N:13]([C@H:17]4[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]4)[CH2:14][CH2:15][O:16][C:11]=3[CH:10]=2)O1.[CH2:27]([N:31]1[CH:36]=[CH:35][C:34](OS(C(F)(F)F)(=O)=O)=[C:33]([Cl:45])[C:32]1=[O:46])[CH2:28][CH2:29][CH3:30].C([O-])(O)=O.[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:27]([N:31]1[CH:36]=[CH:35][C:34]([C:9]2[CH:25]=[CH:24][C:12]3[N:13]([CH:17]4[CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH2:22]4)[CH2:14][CH2:15][O:16][C:11]=3[CH:10]=2)=[C:33]([Cl:45])[C:32]1=[O:46])[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 25221428Trifluoromethanesulfonic acid 1-butyl-3-chloro-2-oxo-1,2-dihydropyridin-4-yl esterHCID 178431016HCID 178431016, compound

Product 1

HCID 585053101-Butyl-3-chloro-4-[4-(4-oxo-cyclohexyl)-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl]-1H-pyridin-2-oneYield 15.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of intermediate D15 (0.15 g, 0.418 mmol), intermediate D4 (0.139 g, 0.418 mmol), tetrakis(triphenylphosphine)palladium(0) (0.0241 g, 0.0209 mmol) and an aqueous saturated NaHCO3 solution (1 ml) in dioxane (4 ml), was heated at 150° C. for 10 min. under microwave irradiation. After cooling to r.t., the r.m. was filtered through diatomaceous earth, treated with EtOAc and the organic layer was washed with water and then with brine. The organic fraction was dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-10% EtOAc/DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield D23 (0.027 g, 15.59%).

Workup

  1. filtrationwas filtered through diatomaceous earth
  2. additiontreated with EtOAc
  3. washthe organic layer was washed with water
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe crude residue was purified by column chromatography (silica gel; 0-10% EtOAc/DCM as eluent)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-edda7789c415415287c15406eebff1f6
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

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