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

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	2-Thiazolamine, 4-(trifluoromethyl)-	HCID 1201417	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
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-(trifluoromethyl)-1,3-thiazol-2-yl]acetamide	HCID 46927022	—

Reaction Steps

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (100 mg, 0.393 mmol) with 4-(trifluoromethyl)-1,3-thiazol-2-amine (66 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.471 mmol), HOBt (16 mg, 0.118 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (4 ml) to give 27 mg of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.18 (s, 3H), 3.46 (s, 3H), 4.05 (s, 2H), 7.07 (s, 1H), 7.91 (s, 1H), 12.70 (br s, 1H); APCI-MS (m/z) 404.97 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987278B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-f2f002be385c43dab5743f6b12e5841b
Source note	uspto-grants-2015_03