2-Thiophenecarbonyl chloride → HCID 68406166, Verbindung

HRID 1713970

Reaktionsgleichung

Reaktionsgleichung von HRID 1713970
[CH2:1]1[CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:5]([C:6](=O)[CH2:7]Br)=[CH:4][C:3]=2[O:2]1.[N:15]1([CH2:21][CH2:22][CH2:23][NH:24][C:25]([NH2:27])=[S:26])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42](Cl)=[O:43]>C(O)C>[O:13]1[CH2:14][CH2:1][O:2][C:3]2[CH:4]=[C:5]([C:6]3[N:27]=[C:25]([N:24]([CH2:23][CH2:22][CH2:21][N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)[C:42]([C:38]4[S:37][CH:41]=[CH:40][CH:39]=4)=[O:43])[S:26][CH:7]=3)[CH:10]=[CH:11][C:12]1=2

Komponenten

6

Edukt 4

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 2760135N-[3-(4-Morpholinyl)propyl]thioureaHCID 27761712-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one

Produkt 1

HCID 68406166HCID 68406166, VerbindungAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3,4-(ethylenedioxy)phenacyl bromide (77 mg, 0.3 mmol) and (3-morpholin-4-yl-propyl)-thiourea (61 mg, 0.3 mmol) in dry ethanol (3 mL) was heated at reflux for 10 min, cooled to room temperature, and concentrated in vacuo. The resulting residue was suspended in dichloromethane (3 mL) followed by the addition of N,N-diisopropylethylamine (105 μL, 0.6 mmol) and thiophene-2-carbonyl chloride (34 μL, 0.32 mmol). The reaction mixture was maintained at room temperature overnight, then concentrated in vacuo. The resulting residue was dissolved in DMSO (1.5 mL) and subjected to HPLC purification (Method Y). The resulting free amine was dissolved in MeOH (1 mL) and 1M HCl/ether (50 mL) was added. The precipitate was filtered and dried in vacuo to provide the title compound (72 mg) as an off-white solid as the hydrochloride salt. LC/MS (ESI) m/z 472.3 [M+H]. HPLC retention time (Method A)=2.72 min.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 10 min
  3. concentrationconcentrated in vacuo
  4. temperatureThe reaction mixture was maintained at room temperature overnight
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting residue was dissolved in DMSO (1.5 mL)
  7. customsubjected to HPLC purification (Method Y)
  8. dissolutionThe resulting free amine was dissolved in MeOH (1 mL)
  9. addition1M HCl/ether (50 mL) was added
  10. filtrationThe precipitate was filtered
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c99c75df6de14304bf94cbac0685eeae
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795290B2

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