Triethylamine → 2-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-N-(1-methyl-1-phenylethyl)-1,3-thiazole-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Cumylamine	HCID 68509	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid	HCID 25126134	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-N-(1-methyl-1-phenylethyl)-1,3-thiazole-5-carboxamide	HCID 59208455	—

Reaction Steps

HATU (0.078 mg, 0.225 mmol) was added to a solution of 2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid (Example 17, 60 mg, 0.205 mmol), Et3N (84 μL, 0.41 mmol) and cumylamine (28 mg, 0.205 mmol) in 3 mL DMF. After stirring at room temperature for two hours, the mixture was diluted with water and extracted with EtOAc. The product precipitated during the workup and it was collected by filtration, washed with water and EtOAc and dried (20 mg). MS (ESP): 410 (M+H+) for C21H23N5O2S.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07674801B2
Source dataset	uspto-grants-2010_03
ORD ID	ord-409de890c2584456b9e4a1b949e4c50c
Source note	uspto-grants-2010_03