Tetrahydrofuran → HCID 46833855, compound

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	3-Chloro-5-(trifluoromethyl)-2-pyridinamine	HCID 607248	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	6-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid	HCID 68407345	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 46833855	HCID 46833855	—

Reaction Steps

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 7A (100 mg, 0.236 mmol) with 3-chloro-5-(trifluoromethyl)pyridin-2-amine (51 mg, 0.260 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol) and DMAP (27 mg, 0.236 mmol) in the mixture of THF and DMF (1:1, 6 mL) to give 25 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (s, 9H), 3.57 (s, 2H), 7.16 (t, J=73.5 Hz, 1H), 7.20-7.46 (m, 3H), 7.53-7.62 (m, 2H), 7.88 (d, J=15.9 Hz, 1H), 8.09 (s, 1H), 8.57 (s, 1H), 8.86 (s, 1H), 11.12 (br s, 1H); APCI-MS (m/z) 601.30 (MH)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318928B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-01b682b25e2c4a5b958eacefb47af0f4
Source note	uspto-grants-2012_11