1,2-Dichloroethane → 3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-N-piperidin-2-ylmethyl-benzamide

HRID 14761

Reaktionsgleichung

Reaktionsgleichung von HRID 14761
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=O)[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.C(OC([N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[CH2:39][NH2:40])=O)(C)(C)C.C(Cl)CCl>CN(C=O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([NH:40][CH2:39][CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][NH:33]3)=[O:22])[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylateHCID 670445203-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

Produkt 1

HCID 586035553-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-N-piperidin-2-ylmethyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Intermediate 9 (1 mmol) was coupled with 2-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (3 mmol) using EDC (2 mmol) in DMF (10 mL). The DMF was removed by rotary evaporation and the residue purified by flash chromatography on silica gel (ethyl acetate as eluent.) The resulting product was deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 432. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.5-8.65 (m, 2H) 8.38 (m, 1H) 8.22 (m, 1H) 7.95 (m, 1H) 7.55 (m, 1H) 7.28 (m, 1H) 7.20 (d, 1H) 7.05 (d, 2H) 6.68 (d, 2H) 3.5 (m, 2H) 3.3 (m, 2H) 2.95 (m, 1H) 2.6-2.85 (m, 3H) 2.48 (m, 1H) 1.0-1.7 (m, 6H).

Aufarbeitung

  1. customThe DMF was removed by rotary evaporation
  2. customthe residue purified by flash chromatography on silica gel (ethyl acetate as eluent.) The resulting product

Quellen und Nachweise

ORD-Eintrag
ord-96a7a6d2860e45e4bb93749ba9697cf2
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732444B2

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