Triethylamine → [2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethyl]-pyrimidin-2-yl-amine hydrochloride salt

HRID 902697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902697
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:38]=[CH:39][CH:40]=1)[O:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[C:28]=1[Cl:37])[CH2:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl[C:42]1[N:47]=[CH:46][CH:45]=[CH:44][N:43]=1.C(N(CC)CC)C>C(O)C>[ClH:37].[Cl:37][C:28]1[C:29]([C:33]([F:34])([F:35])[F:36])=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][N:11]([CH2:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:42]2[N:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[CH:40]=[CH:39][CH:38]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 59701396HCID 59701396, Verbindung

Produkt 1

HCID 69252291[2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethyl]-pyrimidin-2-yl-amine hydrochloride salt

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirring solution of {3-[3-(2-amino-ethyl)-phenoxy]-propyl}-(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amine (57 mg, 0.1 mml, Example 150) and 2-Chloro-pyrimidine (97 mg, 0.85 mmol) in ethanol (10 mL) was added triethylamine (0.5 ml, 3.75 mmol). The resulting solution was refluxed for 72 hours and then concentrated in vacuo. Purification by preparative HPLC (YMC 75×30 mm, 25 m/min, 95-100% CH3CN) afforded the desired pyrimidine product. The free base was treated with 1 M HCl in Et2O (0.1 ml) and the mixture was concentrated in vacuo to afford the title compound as a solid, 44 mg (64%). MS(ES) m/e 645.4 (M+).

Aufarbeitung

  1. temperatureThe resulting solution was refluxed for 72 hours
  2. concentrationconcentrated in vacuo
  3. customPurification by preparative HPLC (YMC 75×30 mm, 25 m/min, 95-100% CH3CN)

Quellen und Nachweise

ORD-Eintrag
ord-19579e3047e24962b0006bdb59b13099
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365085B2

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