Pyridine → 2-{[2-(4-Trifluoromethoxyphenoxy)-acetylamino]-methyl}thiazole-4-carboxylic acid [2-(3-chlorophenyl)-ethyl]amide

HRID 1009196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009196
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]=[C:15]([CH2:18][NH2:19])[S:16][CH:17]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1.[F:20][C:21]([F:35])([F:34])[O:22][C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29](Cl)=[O:30])=[CH:25][CH:24]=1.N1C=CC=CC=1.[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]=[C:15]([CH2:18][NH:19][C:29](=[O:30])[CH2:28][O:27][C:26]3[CH:32]=[CH:33][C:23]([O:22][C:21]([F:34])([F:20])[F:35])=[CH:24][CH:25]=3)[S:16][CH:17]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 27773084-(Trifluoromethoxy)phenoxyacetyl chlorideHCID 577870612-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide

Produkt 1

HCID 116492242-{[2-(4-Trifluoromethoxyphenoxy)-acetylamino]-methyl}thiazole-4-carboxylic acid [2-(3-chlorophenyl)-ethyl]amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide (0.54 g, 1.8 mmol) was dissolved in methylene chloride (15 mL). (4-Trifluoromethoxyphenoxy)-acetyl chloride (0.47 g, 1.8 mmol) was added followed by pyridine (0.3 mL, 4 mmol) and DMAP (0.02 g, 0.1 mmol). The mixture was stirred for 12 hours. Saturated, aqueous NH4Cl was added and the mixture was extracted with methylene chloride ×3. The combined organic extracts were washed with 1N HCl, saturated, aqueous NaHCO3, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The material was purified by recrystallization from ethanol/diethyl ether to afford the title compound (0.65 g, 68% from the Boc protected amine): 1H NMR (400 MHz, d6-DMSO): 9.08 (t, 1H), 8.40 (t, 1H), 8.10 (s, 1H), 7.27 (m, 5H), 7.17 (d, 1H), 7.06 (d, 2H), 4.65 (s, 2H), 4.62 (d, 2H), 3.48 (m, 2H), 2.84 (t, 2H); MS (ESI-LCMS) for C22H20ClF3N3O4S: 514 (MH+).

Aufarbeitung

  1. extractionthe mixture was extracted with methylene chloride ×3
  2. washThe combined organic extracts were washed with 1N HCl
  3. dry with materialsaturated, aqueous NaHCO3, brine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe material was purified by recrystallization from ethanol/diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-11890b3697214923a219aecc93b4e47c
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973061B2

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