2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile → HCID 135544057, Verbindung

HRID 748533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748533
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)#[N:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][N:28]=1)[C:17]([N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)=[O:18]>>[ClH:13].[OH:12][C:7]1[NH:8][C:9]2[C:5]([C:6]=1[C:27]1[CH:26]=[C:16]([C:17]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[O:18])[CH:15]=[CH:14][N:28]=1)=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2

Komponenten

3

Edukt 2

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 252192501-(2-Chloroisonicotinoyl)-4-methylpiperazine

Produkt 1

HCID 135544057HCID 135544057, VerbindungAusbeute 2 %

Versuchsvorschrift

The reaction was performed as described in Example 49 using 5-cyanooxindole and 1-(2-chloroisonicotinoyl)-4-methylpiperazine. The crude product was purified on a silica gel column using chloroform/ethanol/conc. NH3(aq), (100:10:1), as the eluent. The base (20 mg) was dissolved in chloroform and a solution of HCl in diethyl ether was added until acidic pH. The formed precipitation was filtered and washed with diethyl ether. Drying in vacuo afforded 10 mg the title compound as a red solid. Yield: 2%: 1H NMR (D2O, 400 MHz) δ 7.82-7.77 (m, 1 H), 7.18-7.11 (m, 1 H), 7.09-7.05 (m, 1 H), 7.04-6.98 (m, 1 H), 6.78-6.71 (m, 1 H), 6.67-6.61 (m, 1 H), 4.05-3.94 (m, 1 H), 3.93-3.82 (m, 1 H), 3.67-3.48 (m, 2 H), 3.48-3.37 (m, 1 H), 3.35-3.04 (m, 3 H), 2.92-2.80 (m, 3 H); MS (TSP) m/s 362 (M++1).

Aufarbeitung

  1. customThe crude product was purified on a silica gel column
  2. dissolutionThe base (20 mg) was dissolved in chloroform
  3. additiona solution of HCl in diethyl ether was added until acidic pH
  4. customThe formed precipitation
  5. filtrationwas filtered
  6. washwashed with diethyl ether
  7. customDrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3f270597c0904e46ba87a2e15c645233
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399780B2

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