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 885069ノート

反応式

HRID 885069 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6270a4a58200482ea49ccd8f75c95c42
出典データセット
uspto-grants-2012_08
特許番号
US08242124B2

反応ノート

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