Ethyl Acetate → {5-[(6-Methyl-4'-trifluoromethylbiphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-butyl ester

HRID 1814781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814781
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:17])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:28][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([C:45](Cl)=[O:46])[C:34]=1[C:35]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=1.C(OCC)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:45]([C:33]3[C:34]([C:35]4[CH:40]=[CH:39][C:38]([C:41]([F:42])([F:44])[F:43])=[CH:37][CH:36]=4)=[C:29]([CH3:28])[CH:30]=[CH:31][CH:32]=3)=[O:46])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 110556396-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid chlorideHCID 42609144tert-butyl N-(5-amino-2,3-dihydro-1H-inden-2-yl)carbamate

Produkt 1

HCID 69700046{5-[(6-Methyl-4'-trifluoromethylbiphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (5-amino-indan-2-yl)-carbamic acid tert-butyl ester (12.5 mmol) in methylene chloride (75 mL) is added diisopropylethyl amine (3.3 g, 25 mmol) followed by a solution of 6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carboxylic acid chloride (12.6 mmol) in methylene chloride. After stirring 16 h, the reaction mixture is poured into ethyl acetate and washed with 1N HCl, NaHCO3 solution, and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give a solid. Recrystallization from toluene gives {5-[(6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-butyl ester.

Aufarbeitung

  1. washwashed with 1N HCl, NaHCO3 solution, and brine
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a solid
  5. customRecrystallization from toluene

Quellen und Nachweise

ORD-Eintrag
ord-973b206b679a44c2a405d8227dbdd3a3
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06878707B2

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