Dimethyl Sulfoxide → 9-Cyano-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52560

反応式

HRID 52560 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[Cl-].[NH4+:23].[CH3:24]S(C)=O>>[C:24]([C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23)#[N:23]

参加物

4

反応物 3

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 10066635Methyl 2-(9-bromo-2,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[1,2,3-de]quinoxalin-5-yl)acetate

生成物 1

HCID 542872669-Cyano-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione収率 39%

反応条件

温度
180 °C

実験手順

A mixture of 9-bromo-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (530 mg, 1.50 mmol) and cuprous cyanide (890 mg, 9.9 mmol) in dimethyl sulfoxide (5 mL) was heated at 180° C. for 8.5 h and poured into 1N aqueous ammonium chloride (200 mL). The mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL). The extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL), dried over magnesium sulfate, and concentrated. The residue was rinsed with dichloromethane to give 176 mg of the title compound (39%): mp 255°~258° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.22 (bs, 1H), 7.47 (d, 1H, J=2 Hz), 7.31 (d, 1H, J=2 Hz), 5.02~5.16 (m, 1H), 3.63 (s, 3H), 2.95 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.85 (dm, 1H, J=17.1 Hz), 2.55~2.72 (m, 2H), 2.15 (dm, 1H, J=13.5 Hz), 1.80~1.98 (m, 1H).

後処理

  1. extractionThe mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL)
  2. washThe extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was rinsed with dichloromethane

出典と根拠

ORDレコード
ord-caf0fd363b4a4aef99d8f4f977e48233
出典データセット
uspto-grants-1997_04
特許番号
US05616586

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