Acetic Acid → Ethyl 3-(5-(2-(((2-chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405253
[CH:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:21])=[N:18][CH:19]=1)=O.[Cl:30][C:31]1[CH:36]=[C:35]([NH2:37])[CH:34]=[CH:33][C:32]=1[C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=1.CC(O)=O.[BH3-]C#N.[Na+].[NH4+].[Cl-]>CCO>[Cl:30][C:31]1[CH:36]=[C:35]([NH:37][CH2:1][C:3]2[C:8]([CH3:9])=[CH:7][C:6]([C:10]([F:12])([F:13])[F:11])=[CH:5][C:4]=2[C:14]2[CH:15]=[CH:16][C:17]([C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:21])=[N:18][CH:19]=2)[CH:34]=[CH:33][C:32]=1[C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:45])([F:46])[F:47])=[CH:40][CH:39]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 688342842-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amineHCID 86674283Ethyl 3-(5-(2-formyl-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Produkt 1

HCID 86674284Ethyl 3-(5-(2-(((2-chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl 3-(5-(2-formyl-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (37 mg, 0.09 mmol), 2-chloro-4′-(trifluoromethyl)-[1,1-biphenyl]-4-amine (39 mg, 0.14 mmol) and HOAc (5 μL, 0.09 mmol) were dissolved in EtOH (2 mL) and the resulting mixture was heated to 80° C. After 5 h the resulting mixture was cooled to room temperature, solid NaCNBH3 (28 mg, 0.45 mmol) was added and the resulting mixture was stirred at room temperature. After 2 h saturated aqueous NH4Cl was added and the aqueous phase was extracted with EtOAc. The combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Aufarbeitung

  1. temperatureAfter 5 h the resulting mixture was cooled to room temperature
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-28a5570787624e5a932a57911170a02c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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