Tyramine → 4-(2-{4-[3-(Pyrrolidin-3-ylamino)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

HRID 14746

Reaktionsgleichung

Reaktionsgleichung von HRID 14746
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][N:23]=[C:22](Cl)[N:21]=3)[CH:15]=2)[CH2:9]1)=O)(C)(C)C.[NH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1>>[NH:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:27][CH2:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=4)[N:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:9]1

Komponenten

3

Edukt 2

HCID 5610TyramineHCID 866032463-[3-(2-Chloro-pyrimidin-4-yl)-phenylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 586034854-(2-{4-[3-(Pyrrolidin-3-ylamino)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Versuchsvorschrift

Intermediate 8b was coupled with tyramine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 376. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.2 (d, 1H) 7.0-7.5 (m, 4H) 6.9 (d, 1H) 6.68 (d, 2H) 5.05 (m, 1H) 4.28 (m, 1H) 3.8 (m, 2H) 3.2-3.6 (m, 4H) 2.9 (m, 2H) 2.0-2.6 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-22de289468744e0c87c1670893bf0e97
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732444B2

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