Acetamide, 2-cyano-N-phenyl- → tert-butyl 3-cyano-2-oxo-1-phenyl-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 885069노트

반응식

HRID 885069 반응식
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].[Li+].CC([N-]C(C)C)C.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31](=O)/[C:30](=[CH:35]/N(C)C)/[CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[C:1]([C:3]1[C:4](=[O:5])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:31]2[CH2:32][CH2:33][N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[CH2:29][C:30]=2[CH:35]=1)#[N:2]

참가 물질

5

반응물 3

HCID 69296Acetamide, 2-cyano-N-phenyl-HCID 2724682Lithium diisopropylamideHCID 10610967tert-butyl (3E)-3-[(dimethylamino)methylidene]-4-oxopiperidine-1-carboxylate

생성물 1

HCID 58026066tert-butyl 3-cyano-2-oxo-1-phenyl-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-Cyano-N-phenylacetamide (820 mg) in THF (20 mL) was treated with LDA (4.4 mL, 1.8M solution in heptane/THF/ethylbenzene) at −78° C. for 1 h, before (E)-tert-butyl-3-((dimethylamino)methylene)-4-oxopiperidine-1-carboxylate (1 g) was added. The reaction mixture was allowed to warm to room temperature, and quenched with saturated NaHCO3 aqueous solution (20 mL). The aqueous solution was extracted with EtOAc (3×20 mL) and the combined organic layer was dried over MgSO4. Concentration under vacuum provided a residue which was purified by HPLC to afford tert-butyl 3-cyano-2-oxo-1-phenyl-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate. LCMS: m/z 352.2 (M+H)+, 1.63 min (method 8). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.19 (s, 1H) 7.48-7.57 (m, 3H) 7.33 (d, J=7.02 Hz, 2H) 4.33 (s, 2H) 3.44 (t, J=5.65 Hz, 2H) 2.19 (t, J=5.80 Hz, 2H) 1.39 (s, 9H).

후처리

  1. additionwas added
  2. customquenched with saturated NaHCO3 aqueous solution (20 mL)
  3. extractionThe aqueous solution was extracted with EtOAc (3×20 mL)
  4. dry with materialthe combined organic layer was dried over MgSO4
  5. concentrationConcentration under vacuum
  6. customprovided a residue which
  7. customwas purified by HPLC

출처 및 근거

ORD 기록
ord-6270a4a58200482ea49ccd8f75c95c42
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242124B2

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