Sodium Carbonate → 3-{(S)-1-[4-(1,5-Dimethyl-6-oxo-1,6-dihydro-pyridazin-3-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

HRID 2037824노트

반응식

HRID 2037824 반응식
C([O-])([O-])=O.[Na+].[Na+].[OH:7][C:8]([CH3:41])([CH3:40])[CH2:9][C@@:10]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:15][C:14](=[O:16])[N:13]([C@H:17]([C:19]2[CH:24]=[CH:23][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:21][CH:20]=2)[CH3:18])[CH2:12][CH2:11]1.Cl[C:43]1[CH:44]=[C:45]([CH3:51])[C:46](=[O:50])[N:47]([CH3:49])[N:48]=1>CN(C)C=O>[CH3:49][N:47]1[C:46](=[O:50])[C:45]([CH3:51])=[CH:44][C:43]([C:22]2[CH:21]=[CH:20][C:19]([C@@H:17]([N:13]3[CH2:12][CH2:11][C@:10]([CH2:9][C:8]([OH:7])([CH3:40])[CH3:41])([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:15][C:14]3=[O:16])[CH3:18])=[CH:24][CH:23]=2)=[N:48]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-oneHCID 598459736-Chloro-2,4-dimethylpyridazin-3(2H)-one

생성물 1

HCID 426054993-{(S)-1-[4-(1,5-Dimethyl-6-oxo-1,6-dihydro-pyridazin-3-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

2 M aqueous Na2CO3 solution (0.31 mL) was added to a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one (0.15 g) and 6-chloro-2,4-dimethyl-2H-pyridazin-3-one (75 mg) in dimethylformamide (1 mL). The resulting mixture was sparged with argon for 10 min, before [1,1-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (15 mg) was added. The mixture was heated to 100° C. and stirred at this temperature overnight. After cooling to ambient temperature, water was added, and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2→80:20) to afford the title compound.

후처리

  1. customThe resulting mixture was sparged with argon for 10 min, before [1,1-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (15 mg)
  2. additionwas added
  3. temperatureAfter cooling to ambient temperature
  4. additionwater was added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2→80:20)

출처 및 근거

ORD 기록
ord-f532e44237194f0eb63c9dd5f8d0cbfc
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575156B2

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