2-(Trifluoromethyl)benzylamine → 3-amino-N-(2-(trifluoromethyl)benzyl)cyclohexanecarboxamide

Participants

Role	Name	HCID	Charge
Reactant	2-(Trifluoromethyl)benzylamine	HCID 76447	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid	HCID 4420316	—
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	—
Product	3-amino-N-(2-(trifluoromethyl)benzyl)cyclohexanecarboxamide	HCID 59448247	—

Reaction Steps

To a solution of 3-(Boc-amino)cyclohexanecarboxylic acid (500 mg, 2.055 mmol, 1 equivalent) in dimethylformamide (10 ml) was added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 781 mg, 2.055 mmol, 1 equivalent) and diisopropylethylamine (0.716 ml, 4.11 mmol, 2 equivalents). 2-trifluoromethyl benzylamine (360 mg, 2.055 mmol, 1 equivalent) was added and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated to give the crude product, which was purified with RP-HPLC. The purified compound was treated with 50% TFA in DCM (20 ml) at room temperature for 2 hours, and then the solvents were removed in vacuo. The product (103 mg, 12% yield) was carried onto the next step without further purification. MS (ES+): m/e 301.06 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07994317B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-74602e20f4fe4818a11231872e75c4bb
Source note	uspto-grants-2011_08