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

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	4-[3-(Trifluoromethoxy)phenyl]-1,3-thiazol-2-amine	HCID 2760731	—
Reactant	1,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione	HCID 71008093	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	1,2-Dichloroethane	HCID 11	—
Product	2-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[3-(trifluoromethoxy)phenyl]-1,3-thiazol-2-yl}acetamide	HCID 46927771	—

Reaction Steps

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (150 mg, 0.590 mmol) with 4-[3-(trifluoromethoxy)phenyl]-1,3-thiazol-2-amine (155 mg, 0.590 mmol) in the presence of EDCI hydrochloride (135 mg, 0.708 mmol), HOBt (24 mg, 0.177 mmol) and DMAP (7.21 mg, 0.059 mmol) in 1,2 dichloroethane (6 ml) to give 40 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), 7.32 (d, J=7.8 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.78 (s, 1H), 7.87 (s, 1H), 7.94 (d, J=8.1 Hz, 1H), 12.44 (br s, 1H); ESI-MS (m/z) 497.03 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08507503B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-d7319ed7456044f9bda5fc5b4559d913
Source note	uspto-grants-2013_08