Cyclohexylamine → 5-Bromo-N-cyclohexylpyridine-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Cyclohexylamine	HCID 7965	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	5-Bromonicotinic acid	HCID 88707	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	5-Bromo-N-cyclohexylpyridine-3-carboxamide	HCID 4800029	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution of 5-bromonicotinic acid (XLII) (500 mg, 2.49 mmol) in DMF (8 mL) was added cyclohexanamine (XLIII) (247 mg, 2.49 mmol) and DIPEA (643 mg, 4.98 mmol). The reaction was cooled at 0° C. before adding HATU (947 mg, 2.49 mmol). The reaction was warmed to room temperature and stirred for 4 hrs. The reaction was diluted with EtOAc, washed with 2× water, brine, dried over MgSO4 and concentrated under vacuum to yield crude 5-bromo-N-cyclohexylnicotinamide (XLIV). The product was used without further purification. ESIMS found for C12H15BrN2O m/z 283 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08697887B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-f9d883a803e645059b07c195cf68b4fe
Source note	uspto-grants-2014_04