Triethylamine → N,4-Dibenzyl-2-(3-phenylpropanamido)thiazole-5-carboxamide

HRID 45386

Reaktionsgleichung

Reaktionsgleichung von HRID 45386
[NH2:1][C:2]1[S:3][C:4]([C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=1.[C:24](Cl)(=[O:33])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>O1CCCC1.CN(C1C=CN=CC=1)C>[CH2:17]([NH:16][C:14]([C:4]1[S:3][C:2]([NH:1][C:24](=[O:33])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:6][C:5]=1[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 866425132-Amino-4-benzylthiazole-5-carboxylic Acid Benzylamide

Produkt 1

HCID 59369667N,4-Dibenzyl-2-(3-phenylpropanamido)thiazole-5-carboxamideAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-N,4-dibenzylthiazole-5-carboxamide (0.053 g, 0.16 mmol) in tetrahydrofuran (5 mL) at 0° C. was added hydrocinnamoyl chloride (0.03 mL, 0.20 mmol), DMAP (cat.) and triethylamine (0.3 mL, 2.10 mmol). The reaction mixture was allowed to warm to ambient temperature over 18 h then concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford the title compound in 49% yield (0.036 g); 1H NMR (CDCl3, 400 MHz) δ 7.35-7.15 (m, 15H), 4.56 (d, J=5.6 Hz, 2H), 4.37 (s, 2H), 3.03 (t, J=7.6 Hz, 2H), 2.74 (t, J=7.6 Hz, 2H); MS (ES+) m/z 456 (M+1).

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customThe crude product was purified by flash column chromatography
  3. washeluting with ethyl acetate/hexanes (5/95 to 100/0)

Quellen und Nachweise

ORD-Eintrag
ord-a65c26be2f2a45539afc30bec31cdf56
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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