Pyridine → N-Benzyl-4-methyl-2-(5-phenylpentanamido)thiazole-5-carboxamide

HRID 45379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45379
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][C:34](Cl)=[O:35])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1.ClCCl.CN(C1C=CC=CN=1)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 109654605-phenylpentanoyl Chloride

Produkt 1

HCID 59369684N-Benzyl-4-methyl-2-(5-phenylpentanamido)thiazole-5-carboxamideAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 218852-DimethylaminopyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled mixture of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.10 g, 0.40 mmol), pyridine (0.096 g, 1.21 mmol), and dimethylaminopyridine (0.010 mg) in anhydrous tetrahydrofuran (5 mL) was added 5-phenylpentanoyl chloride (0.16 g, 0.81 mmol) in anhydrous dichloromethane (1 mL) dropwise. The reaction mixture was stirred at ambient temperature for 2 hours, then diluted with dichloromethane (10 mL) and washed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrate in vacuo. The residue was purified by column chromatography over silica gel, eluting with ethyl acetate/hexanes (1/1) to afford the title compound as a clear oil (0.16 g, 97%) %); 1H NMR (CDCl3, 300 MHz) δ 11.19 (s, br, 1H), 7.33-7.09 (m, 10H), 6.40 (t, J=4.8 Hz, 1H), 4.58 (d, J=5.8 Hz, 2H), 2.60-2.39 (m, 7H), 1.74-1.56 (m, 4H); MS (ES+) m/z 408.6 (M+1).

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrate in vacuo
  5. customThe residue was purified by column chromatography over silica gel
  6. washeluting with ethyl acetate/hexanes (1/1)

Quellen und Nachweise

ORD-Eintrag
ord-d47a195e5c63486b8f9d6aa68013c626
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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