2-Amino-5-cyanopyridine → HCID 46833854, compound

Participants

Role	Name	HCID	Charge
Reactant	2-Amino-5-cyanopyridine	HCID 818260	—
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	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 46833854	HCID 46833854	—

Reaction Steps

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 7A (80 mg, 0.189 mmol) with 6-aminonicotinonitrile (27 mg, 0.226 mmol) in the presence of EDCI hydrochloride (72 mg, 0.378 mmol), DMAP (22 mg, 0.189 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 25 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.03 (s, 9H), 3.56 (s, 2H), 7.17 (t, J=74.1 Hz, 1H), 7.19-7.25 (m, 2H), 7.42-7.50 (m, 2H), 7.55-7.62 (m, 1H), 7.82 (d, J=15.6 Hz, 1H), 8.02-8.08 (m, 1H), 8.18-8.24 (m, 1H), 8.28-8.35 (m, 1H), 8.83-8.90 (m, 1H), 11.39 (br s, 1H); APCI-MS (m/z) 524.25 (MH)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318928B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-2c72173970e84b4dbceabe3577dbf20a
Source note	uspto-grants-2012_11