2-Thiophenecarbonyl chloride → HCID 68406167, Verbindung

HRID 1713971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713971
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14])=O.[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]>O1CCOCC1>[CH3:14][O:13][C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[C:3]1[N:27]=[C:25]([N:24]([CH2:23][CH2:22][CH2:21][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[C:42]([C:38]2[S:37][CH:41]=[CH:40][CH:39]=2)=[O:43])[S:26][CH:2]=1

Komponenten

6

Edukt 4

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 986832-Bromo-1-(2,4-dimethoxyphenyl)ethanoneHCID 2760135N-[3-(4-Morpholinyl)propyl]thiourea

Produkt 1

HCID 68406167HCID 68406167, VerbindungAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-bromo-2′,4′-dimethoxyacetophenone (156 mg, 0.6 mmol) and (3-morpholin-4-yl-propyl)-thiourea (122 mg, 0.6 mmol) in dry dioxane (5 ml) was heated at 80° C. for 2 h, cooled to room temperature, and concentrated in vacuo. The resulting residue was suspended in dichloromethane (5 mL) followed by the addition of N,N-diisopropylethylamine (209 μL, 1.2 mmol) and thiophene-2-carbonyl chloride (96 μL, 0.9 mmol). The reaction mixture was maintained at room temperature overnight, then concentrated in vacuo. The resulting residue was dissolved in DMSO (2.5 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 (207 mg) as an yellow solid as the hydrochloride salt. LC/MS (ESI) m/z 474.3 [M+H]. HPLC retention time (Method A)=2.81 min.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. temperatureThe reaction mixture was maintained at room temperature overnight
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in DMSO (2.5 mL)
  6. customsubjected to HPLC purification (Method Y)
  7. dissolutionThe resulting free amine was dissolved in MeOH (1 mL)
  8. addition1M HCl/ether (50 mL) was added
  9. filtrationThe precipitate was filtered
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e6276033429d4d09be7db005aca18d2c
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795290B2

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