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

HRID 240316

반응식

HRID 240316 반응식
[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]

참가 물질

4

반응물 3

HCID 3776IsopropanolHCID 2723951DiaminomaleonitrileHCID 57831019HCID 57831019, 화합물

생성물 1

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

반응 조건

온도
80 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-2ecba929284b42688b3bc34e18d072dc
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648076B2

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