Diisopropylethylamine → 1-Acetyl-N-(3-(N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamido)propyl)piperidine-4-carboxamide

HRID 2218513

Reaktionsgleichung

Reaktionsgleichung von HRID 2218513
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C:13]1[S:14][CH:15]=[C:16]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[CH:22]=2)[N:17]=1)[C:6]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)=[O:7].C(N(CC)C(C)C)(C)C.[C:36]([N:39]1[CH2:47][CH2:46][CH:42]([C:43](Cl)=[O:44])[CH2:41][CH2:40]1)(=[O:38])[CH3:37]>C(Cl)(Cl)Cl>[C:36]([N:39]1[CH2:40][CH2:41][CH:42]([C:43]([NH:1][CH2:2][CH2:3][CH2:4][N:5]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[O:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[CH:22]=3)[N:17]=2)[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[O:7])=[O:44])[CH2:46][CH2:47]1)(=[O:38])[CH3:37]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 68407996N-(3-aminopropyl)-N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamide

Produkt 1

HCID 684062611-Acetyl-N-(3-(N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamido)propyl)piperidine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A mixture of the amine prepared above (77 mg, 0.2 mmol) and N,N-diisopropylethylamine (139 μL, 0.8 mmol) was dissolved in chloroform (2 mL), and a portion of the solution (200 μL, 0.02 mmol) was added to a solution of 1-acetyl-isonipecotoyl chloride (7.6 mg, 0.04 mmol) in chloroform (200 μL). The reaction mixture was maintained at room temperature overnight.). The reaction mixture was maintained at room temperature overnight, then concentrated in vacuo. The resulting residue was dissolved in DMSO (200 μL) and subjected to HPLC purification (Method Z) to provide the title compound (4.5 mg) as a yellowish solid. LC/MS (ESI) m/z 537.1 [M+H]. HPLC retention time (Method C)=3.44 min.

Aufarbeitung

  1. temperatureThe reaction mixture was maintained at room temperature overnight
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in DMSO (200 μL)
  4. customsubjected to HPLC purification (Method Z)

Quellen und Nachweise

ORD-Eintrag
ord-4dfe5492e5094c07ae111d76eb72d2ae
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07410988B2

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