Triethylamine → 3-Methyl-2-[4-(trifluoromethyl)phenyl]-N-[(R)-2-(2-pyridylmethylamino)-5-indanyl]benzamide

HRID 1531303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531303
[NH2:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:11][C:12]([C:14]3[C:15]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=4)=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:8]=2)[CH2:3]1.C(N(CC)CC)C.[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH:44]=O.[BH4-]>CO>[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH2:44][NH:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:11][C:12]([C:14]3[C:15]([C:21]4[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=4)=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:8]=2)[CH2:3]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 142732-PyridinecarboxaldehydeHCID 28123BorohydrideHCID 11112358(r)-n-(2-Aminoindan-5-yl)-6-methyl-4'-trifluoromethylbiphenyl-2-carboxamide

Produkt 1

HCID 98273433-Methyl-2-[4-(trifluoromethyl)phenyl]-N-[(R)-2-(2-pyridylmethylamino)-5-indanyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The amine is dissolved in methanol (160 mL), triethylamine (1.45 g, 14.4 mmol) and 2-pyridinecarboxaldehyde (1.59 g, 14.8 mmol) are added, and the mixture is stirred overnight. Polymer supported borohydride (Aldrich, borohydride on Amberlite IRA-400, 2.5 mmol/g, 6.0 g, 14.8 mmol) is added and the mixture is stirred for an additional 24 hours. The resin is removed by filtration and the filtrate is concentrated in vacuo. The residue is dissolved in a small amount of ethyl acetate and triturated with hexane to yield (R)-6-methyl4′-trifluoromethylbiphenyl-2-carboxylic acid [2-(2-pyridylmethylamino)-indan-5-yl] amide as a solid. The solid is dissolved in ethanol (100 mL) and a saturated solution of HCl (g) in ethyl ether is added. The resulting solid is collected to yield (R)-6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid [2-(2-pyridylmethylamino)-indan-5-yl] amide hydrochloride, m.p. 281-283° C.

Aufarbeitung

  1. additionis added
  2. stirringthe mixture is stirred for an additional 24 hours
  3. customThe resin is removed by filtration
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in a small amount of ethyl acetate
  6. customtriturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-d9717ef8046a43938737f49314a11677
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197798B1

Notizen zur Reaktion

Wird geladen…