1-Hydroxybenzotriazole → HCID 46926944, compound

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	3-(4-chlorophenyl)isoxazol-5-amine	HCID 2104062	—
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	HCID 46926944	HCID 46926944	—

Reaction Steps

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (100 mg, 0.393 mmol) with 3-(4-chlorophenyl)isoxazol-5-amine (76 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol), HOBt (16 mg, 0.118 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (4 ml) to give 50 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.20 (s, 3H), 3.47 (s, 3H), 4.01 (s, 2H), 6.67 (s, 1H), 7.07 (s, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.85 (d, J=8.4 Hz, 2H), 11.90 (br s, 1H); APCI-MS (m/z) 429.17 (M−H)−.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987278B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-50937a29e98f4e73a336dc6dcd14c3c0
Source note	uspto-grants-2015_03