3-Chloro-4-methylphenyl isocyanate → 1-(3-Chloro-4-methylphenyl)-3-(4-((isopropyl(methyl)amino)methyl)thiazol-2-YL)urea

HRID 350958

Reaktionsgleichung

Reaktionsgleichung von HRID 350958
[CH:1]([N:4]([CH2:6][C:7]1[N:8]=[C:9]([NH2:12])[S:10][CH:11]=1)[CH3:5])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([N:21]=[C:22]=[O:23])[CH:17]=[CH:18][C:19]=1[CH3:20]>ClCCl>[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]([NH:12][C:9]2[S:10][CH:11]=[C:7]([CH2:6][N:4]([CH:1]([CH3:3])[CH3:2])[CH3:5])[N:8]=2)=[O:23])[CH:17]=[CH:18][C:19]=1[CH3:20]

Komponenten

4

Edukt 2

HCID 628323-Chloro-4-methylphenyl isocyanateHCID 210906044-((Isopropyl(methyl)amino)methyl)thiazol-2-amine

Produkt 1

HCID 115594151-(3-Chloro-4-methylphenyl)-3-(4-((isopropyl(methyl)amino)methyl)thiazol-2-YL)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-((isopropyl(methyl)amino)methyl)thiazol-2-amine (18 mg, 0.1 mmol) in dichloromethane (0.5 mL) is added to 3-chloro-4-methylphenyl isocyanate (16.7 mg, 0.1 mmol) in dichloromethane (0.5 mL). The resulting reaction mixture is shaken at room temperature for 1 hour. The solvent is evaporated under vacuum. The residue is purified by preparative LC to yield a brown glass LCMS, retention time: 1.87 min, M+H+: 353. H1-NMR (DMSO, σ ppm): 10.82 (s, 1H), 9.51–9.41 (s, br, 1H), 9.31 (s, 1H), 7.70 (s, 1H), 7.33 (s, 1H), 7.18–7.30 (m, 2H), 4.11–4.39 (m, 2H), 2.69 (d, 3H), 2.28 (s, 3H), 1.29 (t, 6H)).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe solvent is evaporated under vacuum
  3. customThe residue is purified by preparative LC
  4. customto yield a brown glass LCMS, retention time: 1.87 min, M+H+

Quellen und Nachweise

ORD-Eintrag
ord-67651169444241a3b9684484ef6235b0
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183300B2

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