Triethylamine → Ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylate

HRID 45403

Reaktionsgleichung

Reaktionsgleichung von HRID 45403
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.C(N(CC)CC)C.Cl.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>O1CCCC1>[C:21]([NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 12262826Isonicotinoyl chloride hydrochloride

Produkt 1

HCID 719362Ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (5.70 g, 30.60 mmol) and triethylamine (10.0 mL, 71.80 mmol) in tetrahydrofuran (100 mL) was added isonicotinoyl chloride hydrochloride (6.00 g, 32.00 mmol). The reaction mixture was stirred at ambient temperature for 2 days. The solvent was removed by evaporation and the resulting white solid was washed sequentially with water, 10% sodium bicarbonate solution, and water, then dried to afford the title compound in 90% yield (8.10 g); 1H NMR (DMSO-d6, 300 MHz) δ 8.77 (d, J=6.0 Hz, 2H), 8.77 (d, J=6.0 Hz, 2H), 4.23 (q, J=7.2 Hz, 2H), 2.34 (s, 3H). 1.27 (t, J=7.2 Hz, 3H); MS (ES+) m/z 292.0 (M+1).

Aufarbeitung

  1. customThe solvent was removed by evaporation
  2. washthe resulting white solid was washed sequentially with water, 10% sodium bicarbonate solution, and water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2a7f7b852a024355ba6a8f13ce27cd05
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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