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Triethylamine → N-{2-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]-oxadiazol-3-yl]-phenyl}-2-(4-methyl-piperazin-1-yl)-acetamide

HRID 2250461
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2250461
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]=[C:12]([C:14]3[S:15][CH:16]=[CH:17][C:18]=3[Cl:19])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.Br[CH2:28][C:29](Br)=[O:30].[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>O1CCCC1.C(O)C.ClCCl>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[N:13]=[C:12]([C:14]3[S:15][CH:16]=[CH:17][C:18]=3[Cl:19])[O:11][N:10]=2)=[CH:3][C:2]=1[NH:1][C:29](=[O:30])[CH2:28][N:36]1[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]1
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Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 61147Bromoacetyl bromideHCID 99956372-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamine

Produkt 1

HCID 16222399N-{2-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]-oxadiazol-3-yl]-phenyl}-2-(4-methyl-piperazin-1-yl)-acetamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-(3-amino-4-chloro-phenyl)-5-(3-chlorothiophen-2-yl)-[1,2,4]-oxadiazole (56.5 mg, 0.181 mmol), triethylamine (75.0 μL, 0.540 mmol), and bromo-acetyl bromide (48.0 μL, 0.549 mmol) and dichloromethane (15.0 mL) was stirred at room temperature for 30 min. The solution was washed with 5% hydrochloric acid solution, dried over sodium sulfate, and rotary evaporated to dryness. To the residue was added ethanol (10 mL), tetrahydrofuran (10 mL), and 1-methyl-piperazine (525 μL, 4.73 mmol) and the resulting solution was refluxed for 20 min under argon. The solution was partitioned between ethyl acetate (25 mL) and 10% sodium bicarbonate (15 mL). The ethyl acetate layer was washed with water (15 mL), dried over sodium sulfate and rotary evaporated to dryness to yield 68.7 mg (84%) of the title compound as a white solid. 1H NMR (CDCl3): 10.04 (s, 1H), 9.25 (d, J=1.92 Hz, 1H), 7.85 (dd, J1=8.24 Hz, J2=1.64 Hz, 1H), 7.60 (d, J=5.22 Hz, 1H), 7.52 (d, J=8.24 Hz, 1H), 7.12 (d, J=5.49 Hz, 1H), 3.24 (s, 2H), 2.73 (s, 4H), 2.57 (s, 4H), 2.35 (s, 3H).

Aufarbeitung

  1. washThe solution was washed with 5% hydrochloric acid solution
  2. dry with materialdried over sodium sulfate
  3. customrotary evaporated to dryness
  4. temperaturethe resulting solution was refluxed for 20 min under argon
  5. customThe solution was partitioned between ethyl acetate (25 mL) and 10% sodium bicarbonate (15 mL)
  6. washThe ethyl acetate layer was washed with water (15 mL)
  7. dry with materialdried over sodium sulfate
  8. customrotary evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b68d6801e6e24e3888c45aef33c1d496
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07317029B2

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