Dimethyl Sulfoxide → (r)-6-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide

HRID 1531289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531289
[CH3:1][O:2][C:3](=[O:15])[NH:4][C@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:14])[CH:11]=2)[CH2:6]1.CS(C)=O.N1C=CC=CC=1.[CH3:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([C:43](Cl)=[O:44])[C:32]=1[C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([NH:4][C@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:43]([C:31]3[C:32]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:40])([F:42])[F:41])=[CH:35][CH:34]=4)=[C:27]([CH3:26])[CH:28]=[CH:29][CH:30]=3)=[O:44])[CH:11]=2)[CH2:6]1)=[O:15]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 110556396-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid chlorideHCID 11413084(R)-Methyl (5-amino-2,3-dihydro-1H-inden-2-yl)carbamate

Produkt 1

HCID 9869236(r)-6-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To an ice bath cooled solution of (R)-(5-aminoindan-2-yl)-carbamic acid methyl ester (9.5 g, 46.1 mmol) prepared as described in example 12 ([α]D=−26.29 (c=9.87 mg/mL, DMSO); mp 144-145° C.) and pyridine (4.48 mL, 55.5 mmol) in 200 mL of methylene chloride is added 6-methyl-4′-trifluoromethyl-biphenyl-2-carboxylic acid chloride (80.5 mL of a 0.63 M solution in methylene chloride, 50.7 mmol). The reaction is stirred for 15 minutes at room temperature. The mixture is washed with 1N HCl, bicarbonate and brine. The organic layer is dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The product is purified by crystallization from ethyl acetate/hexanes (1:2) to give (R)-6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide (the compound of example 13(i)) as a crystalline solid, mp 112-114° C. MS (ES+), m/z469 (M+1); [α]D=−12.85° (c=11.36 mg/ml DMSO).

Aufarbeitung

  1. customprepared
  2. washThe mixture is washed with 1N HCl, bicarbonate and brine
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by crystallization from ethyl acetate/hexanes (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-8ca476066c754413ba74d577d5126846
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197798B1

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