Diisopropylethylamine → N-(4-(2-methylpyridin-4-yl)benzyl)-4-(pyridin-2-yl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-(2-Pyridyl)Benzoic Acid	HCID 821692	—
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	HCID 67208595	HCID 67208595	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(4-(2-methylpyridin-4-yl)benzyl)-4-(pyridin-2-yl)benzamide	HCID 56598231	—

Reaction Steps

To a mixture of (4-(2-methylpyridin-4-yl)phenyl)methanamine 13-3 (10 mg, 0.05 mmol), 4-(pyridin-2-yl)benzoic acid 13-4 (10 mg, 0.05 mmol), and HATU (23 mg, 0.06 mmol) were added N,N-diisopropylethylamine (DIEA, 17 μL, 0.1 mmol) and DMF (0.5 mL). The solution was stirred overnight at room temperature and was subjected directly to reverse phase preparative HPLC to yield N-(4-(2-methylpyridin-4-yl)benzyl)-4-(pyridin-2-yl)benzamide 13 as white powder. MS m/z 380.2 (M+1). 1H NMR 400 MHz (CDCl3) δ 8.65-8.60 (m, 1H), 8.41 (d, 1H), 7.99-7.85 (m, 4H), 7.80-7.70 (m, 2H), 7.65-7.50 (m, 3H), 7.45 (d, 2H), 7.34 (bs, 1H), 7.32-7.27 (m, 2H), 4.66 (d, 2H), 2.56 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181235B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-40f5ecdb97de49ae8c942978e9dda950
Source note	uspto-grants-2015_11