4-Chloro-3-methoxyaniline → 5-(3,4-Dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide

HRID 1793441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1793441
C[Al](C)C.CO[C:7]([CH:9]1[CH2:14][S:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[NH:10]1)=[O:8].[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][C:27]=1[O:33][CH3:34]>>[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:7]([CH:9]2[CH2:14][S:13][CH2:12][CH:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)[NH:10]2)=[O:8])=[CH:28][C:27]=1[O:33][CH3:34]

Komponenten

4

Edukt 3

HCID 131036924-Chloro-3-methoxyanilineHCID 16682925TrimethylaluminumHCID 651713775-(3,4-Dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid methyl ester

Produkt 1

HCID 865972335-(3,4-Dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A 2.0M solution of trimethylaluminum (0.39 ml, 0.78 mmol, 3.5 equivalents) was added to a solution of 5-(3,4-dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid methyl ester (67 mg, 0.22 mmol, 1.0 equivalents) and 4-chloro-3-methoxyaniline (106 mg, 0.68 mmol, 3.0 equivalents). The solution was stirred at 50° C. for 18 hours. The reaction was quenched with 1N NaOH and extracted with dichloromethane. The dichloromethane extracts were dried with MgSO4, filtered and concentrated. The residue was purified on a 1000 micron preparative TLC. 5-(3,4-Dimethoxy-phenyl)-thiomorpholine-3-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide was obtained as a peach solid (71 mg, 76% yield). Analysis H1 NMR (400 MHz, CDCl3): 8.61 (1H, s), 7.58 (1H, m), 7.26 (1H, m), 6.90 (2H, m), 6.78 (1H, d), 4.04 (1H, m), 3.91 (10H, m), 2.98 (1H, m), 2.78 (2H, m), 2.59 (1H, m). MS (LC-MS): Calculated for C20H23ClN2O4S 423.11, found 423.22.

Aufarbeitung

  1. customThe reaction was quenched with 1N NaOH
  2. extractionextracted with dichloromethane
  3. dry with materialThe dichloromethane extracts were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on a 1000 micron preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-98b259cb2faf4ca8837e87a42fc7b395
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07081458B2

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