Homophthalic acid → 2-[(5-Benzylcarbamoyl-4-methylthiazol-2-ylcarbamoyl)methyl]benzoic acid

HRID 45382

Reaktionsgleichung

Reaktionsgleichung von HRID 45382
[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.[C:18](O)(=[O:29])[CH2:19][C:20]1[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:22]([OH:24])=[O:23]>>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:18]([CH2:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([OH:24])=[O:23])=[O:29])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 66643Homophthalic acidHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Produkt 1

HCID 593697052-[(5-Benzylcarbamoyl-4-methylthiazol-2-ylcarbamoyl)methyl]benzoic acidAusbeute 60 %

Versuchsvorschrift

2-Amino-4-methylthiazole-5-carboxylic acid benzylamide (0.25 g, 1.00 mmol) and homophthalic acid (0.18 g, 1.00 mmol) were melted together at 170° C. for 2 hours. A colorless solid formed after the melt was cooled to ambient temperature. The solid was washed with ether (50 mL) and then crystallized from ethyl acetate/methanol to afford the title compound in 60% yield; 1H NMR (DMSO-d6, 300 MHz) δ 12.37 (s, 1H), 8.48 (t, J=5.9 Hz, 1H), 7.88 (dd, J=1.4, 7.6 Hz, 1H), 7.50 (dt, J=1.4, 7.6 Hz, 1H), 7.40-7.15 (m, 7H), 4.34 (d, J=5.9 Hz, 2H), 4.14 (s, 2H), 2.45 (s, 3H); MS (ES+) m/z 410.5 (M+1).

Aufarbeitung

  1. customA colorless solid formed after the melt
  2. washThe solid was washed with ether (50 mL)
  3. customcrystallized from ethyl acetate/methanol

Quellen und Nachweise

ORD-Eintrag
ord-b3c9632dacfb45eb98a0e6ffb42b0eb9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541457B2

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