Thiopheneethanamine → {4-[3-(Piperidin-4-ylamino)-phenyl]-pyrimidin-2-yl}-(2-thiophen-2-yl-ethyl)-amine

HRID 14736

Reaktionsgleichung

Reaktionsgleichung von HRID 14736
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][CH2:34][NH2:35]>>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:35][CH2:34][CH2:33][C:29]4[S:28][CH:32]=[CH:31][CH:30]=4)[N:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:12][CH2:13]1

Komponenten

3

Edukt 2

HCID 116521ThiopheneethanamineHCID 866032444-[3-(2-Chloro-pyrimidin-4-yl)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 58603665{4-[3-(Piperidin-4-ylamino)-phenyl]-pyrimidin-2-yl}-(2-thiophen-2-yl-ethyl)-amine

Versuchsvorschrift

Intermediate 7 was coupled with 2-thiophen-2-yl-ethylamine by procedure F and the resulting product deprotected by procedure G. LC-MS showed the product had the expected M+H+ of 380. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.28 (d, 1H) 6.8-7.5 (m, 8H) 4.85 (m, 1H) 3.9 (m, 2H) 3.7 (m, 2H) 3.1-3.5 (m, 4H) 2.2-2.3 (m, 2H) 2.28 (m, 2H) 1.6-1.8 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-3923cb55a70b494cbee62fcbdec93b23
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732444B2

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