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 2364951노트

반응식

HRID 2364951 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-edda7789c415415287c15406eebff1f6
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697689B2

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