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2-Thiophenecarbonyl chloride → N-(3-Morpholinopropyl)-N-(4-(3-phenylisoxazol-5-yl)thiazol-2-yl)thiophene-2-carboxamide

HRID 1713972
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1713972
Br[CH2:2][C:3]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1)=O.[N:16]1([CH2:22][CH2:23][CH2:24][NH:25][C:26]([NH2:28])=[S:27])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(CC)C(C)C)(C)C.[S:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[C:43](Cl)=[O:44]>O1CCOCC1>[O:19]1[CH2:18][CH2:17][N:16]([CH2:22][CH2:23][CH2:24][N:25]([C:26]2[S:27][CH:2]=[C:3]([C:5]3[O:9][N:8]=[C:7]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:6]=3)[N:28]=2)[C:43]([C:39]2[S:38][CH:42]=[CH:41][CH:40]=2)=[O:44])[CH2:21][CH2:20]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 27355325-(Bromoacetyl)-3-phenylisoxazoleHCID 2760135N-[3-(4-Morpholinyl)propyl]thiourea

Produkt 1

HCID 59769689N-(3-Morpholinopropyl)-N-(4-(3-phenylisoxazol-5-yl)thiazol-2-yl)thiophene-2-carboxamideAusbeute 53,8 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-bromo-1-(3-phenylisoxazol-5-yl)ethan-1-one (160 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 (155 mg) as an off-white solid as the hydrochloride salt. LC/MS (ESI) m/z 481.1 [M+H]. HPLC retention time (Method B)=2.94 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-0d95d6129f614471822fbaaf9c876d53
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07795290B2

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