1-Hydroxybenzotriazole → 2-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	1-Hydroxybenzotriazole	HCID 75771	—
Edukt	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Edukt	4-(3-Fluoro-5-(trifluoromethyl)phenyl)-1,3-thiazol-2-amine	HCID 17774635	—
Edukt	1,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione	HCID 71008093	—
Katalysator	4-(Dimethylamino)pyridine	HCID 14284	—
Lösungsmittel	1,2-Dichloroethane	HCID 11	—
Produkt	2-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide	HCID 46927840	—

Reaktionsschritte

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (100 mg, 0.393 mmol) with 4-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (103 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.471 mmol), HOBt (16 mg, 0.117 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (6 ml) to give 21 mg of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.19 (s, 3H), 3.47 (s, 3H), 4.07 (s, 2H), 7.07 (s, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.97 (s, 1H), 8.06 (d, J=9.0 Hz, 1H), 8.13 (s, 1H), 12.49 (br s, 1H); APCI-MS (m/z) 497.20 (M−H)−.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08987278B2
Quelldatensatz	uspto-grants-2015_03
ORD ID	ord-fd0cca822bb94a2d8894b3e4553463ad
Quellennotiz	uspto-grants-2015_03