Isopropanol → 6-ethyl-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile

HRID 240316

反応式

HRID 240316 の反応式
[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=O)[C:9]2=O)=[CH:5][CH:4]=1)[CH3:2].[NH2:14]/[C:15](/[C:20]#[N:21])=[C:16](\[NH2:19])/[C:17]#[N:18].CC([OH:25])C>>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:25])[C:8]3[C:9]([C:10]=2[CH:11]=1)=[N:14][C:15]([C:20]#[N:21])=[C:16]([C:17]#[N:18])[N:19]=3)[CH3:2]

参加物

4

反応物 3

HCID 3776IsopropanolHCID 2723951DiaminomaleonitrileHCID 57831019HCID 57831019、化合物

生成物 1

HCID 578310246-ethyl-9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile

反応条件

温度
80 °C

実験手順

A suspension of 29c (298 mg, 1.71 mmol) and diaminomaleonitrile (185 mg, 1.71 mmol) in iPrOH (17 ml) was stirred at 80° C. for 20 h. The solvent was evaporated under reduced pressure and the crude was purified by flash chromatography (CH2Cl2). The obtained product was purified by preparative HPLC, obtaining 32 as yellow solid as 7:3 regioisomeric mixture with the 7-ethyl analogue. 1H NMR (300 MHz, CDCl3): main product: δ 7.95 (d, 1H), 7.80 (m, 1H), 7.67 (bd, 1H), 2.83 (q, 2H), 1.33 (t, 3H); minority product: δ 7.89 (d, 1H), 7.89 (m, 1H), 7.56 (bd, 1H), 2.86 (q, 2H), 1.36 (t, 3H). ESI+MS: calcd for C15H8N4O: 260.26; found: 261.1 (MH+).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude was purified by flash chromatography (CH2Cl2)
  3. customThe obtained product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-2ecba929284b42688b3bc34e18d072dc
出典データセット
uspto-grants-2014_02
特許番号
US08648076B2

関連ノート

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