Potassium Carbonate → (R)-3-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-2-yl)oxazolidin-2-one

HRID 2093697

반응식

HRID 2093697 반응식
Br[C:2]1[N:3]([C:7]2[N:16]=[CH:15][C:14]3[N:13]([CH3:17])[C:12](=[O:18])[C@@H:11]([CH2:19][CH3:20])[N:10]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[C:9]=3[N:8]=2)[CH:4]=[CH:5][N:6]=1.[O:26]1[CH2:30][CH2:29][NH:28][C:27]1=[O:31].CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I>[CH:21]1([N:10]2[C:9]3[N:8]=[C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[N:28]4[CH2:29][CH2:30][O:26][C:27]4=[O:31])[N:16]=[CH:15][C:14]=3[N:13]([CH3:17])[C:12](=[O:18])[C@H:11]2[CH2:19][CH3:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 58405307(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

생성물 1

HCID 58405605(R)-3-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-2-yl)oxazolidin-2-one수율 6.4%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 65, 0.11 g, 0.271 mmol), oxazolidin-2-one (35 mg, 0.406 mmol), CuI (10 mg, 0.054 mmol), trans-1,2-bis(methylamino)cyclohexane (15 mg, 0.108 mmol) and K2CO3 (74 mg, 0.542 mmol) were dissolved in 1 mL of dioxane in a screw cap vial and a stream of nitrogen was bubbled through the mixture for 2 minutes. The resulting solution was stirred at 110° C. for 18 h. The reaction mixture filtered and concentrated, then purified by preparative HPLC to give the title compound (7.1 mg). LCMS: 412.2 m/z (M+H)+; ret. Time: 3.24 min (Analytical Method A).

후처리

  1. customcap vial
  2. customa stream of nitrogen was bubbled through the mixture for 2 minutes
  3. filtrationThe reaction mixture filtered
  4. concentrationconcentrated
  5. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-64e1cd46de0c4bedba4d1f1c54be950a
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445503B2

연결된 노트

불러오는 중…