5-Hydroxyindoleacetic Acid → (S)-2-(5-hydroxy-1H-indol-3-yl)-N-(1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethyl)acetamide

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	5-Hydroxyindoleacetic Acid	HCID 1826	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	(S)-1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethanamine	HCID 90281302	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	(S)-2-(5-hydroxy-1H-indol-3-yl)-N-(1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethyl)acetamide	HCID 90281481	—

Reaktionsschritte

(S)-1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethanamine (75 mg, 0.2 mmol), 2-(5-hydroxy-1H-indol-3-yl)acetic acid (47 mg, 0.25 mmol) and HATU (97 mg, 0.26 mmol) were combined in DMF (2 mL) and treated with diisopropylethylamine (70 μL). The reaction was stirred for 30 min and the purified by RP HPLC to provide the title compound: 1H NMR (400 MHz, DMSO-d6) δ 10.53 (d, 1H), 8.67 (d, 1H), 7.58 (s, 1H), 7.38-7.28 (m, 2H), 7.20-7.12 (m, 3H), 7.12-6.98 (m, 4H), 6.91-6.79 (m, 3H), 6.72 (d, 1H), 6.57 (dd, 1H), 5.38-5.31 (m, 1H), 5.17 (d, 2H), 3.71 (s, 3H), 3.40-3.22 (m, 3H), 3.16 (dd, 1H). MS (m/z) 481.2 [M+H]+.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09220710B2
Quelldatensatz	uspto-grants-2015_12
ORD ID	ord-63d7455d3ed0433cbb7d4e53344b85e5
Quellennotiz	uspto-grants-2015_12