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4-(Trifluoromethoxy)benzylamine → 2-[(4-Trifluoromethoxy-benzylamino)-methyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide hydrochloride

HRID 1009203
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1009203
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]([CH2:19][NH2:20])[S:17][CH:18]=2)=[O:13])[CH:6]=[CH:7][CH:8]=1.[F:21][C:22]([F:33])([F:32])[O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]N)=[CH:26][CH:25]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.C(O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]([CH2:19][NH:20][CH2:28][C:27]3[CH:30]=[CH:31][C:24]([O:23][C:22]([F:21])([F:32])[F:33])=[CH:25][CH:26]=3)[S:17][CH:18]=2)=[O:13])[CH:6]=[CH:7][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 5718464-(Trifluoromethoxy)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 673043282-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide hydrochloride

Produkt 1

HCID 673043512-[(4-Trifluoromethoxy-benzylamino)-methyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Katalysator
HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide hydrochloride (0.10 g, 0.3 mmol) and 4-(trifluoromethoxy)benzyl amine (0.06 g, 0.3 mmol) were mixed with sodium cyanoborohydride (1 M in THF, 0.6 mL), ethanol (5 mL), and a catalytic amount of acetic acid (2 drops). The mixture was heated at reflux for 24 hours. The mixture was concentrated in vacuo, diluted with water and extracted with methylene chloride. The combined organic layers were washed with sodium carbonate and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude amine was purified by flash chromatography (EtOAc/hexane), treated with HCl in dioxane, and concentrated in vacuo to afford the title compound: 1H NMR (400 MHz, d6-DMSO): 9.83 (br s, 2H), 8.43 (t, 1H), 8.32 (s, 1H), 7.66 (d, 2H), 7.44 (d, 2H), 7.25 (m, 4H), 4.58 (s, 2H), 4.37 (s, 2H), 3.53 (m, 2H), 2.86 (t, 2H); MS (ESI-LCMS) for C21H20ClF3N3O2S: 470 (MH+).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with methylene chloride
  6. washThe combined organic layers were washed with sodium carbonate and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude amine was purified by flash chromatography (EtOAc/hexane)
  11. additiontreated with HCl in dioxane
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e0fed782977a4e8181fa16522db0bb7c
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973061B2

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