Diisopropylethylamine → 2-(4-(2-methylpyridin-4-yl)phenyl)-N-(6-morpholinopyridin-3-yl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	6-(Morpholino)pyridin-3-amine	HCID 104059	—
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	[4-(2-Methyl-pyridin-4-yl)-phenyl]-acetic acid	HCID 58447644	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(4-(2-methylpyridin-4-yl)phenyl)-N-(6-morpholinopyridin-3-yl)acetamide	HCID 58447751	—

Reaction Steps

A mixture of 2-(4-(2-methylpyridin-4-yl)phenyl)acetic acid 73-1 (40 mg, 0.18 mmol), 6-morpholinopyridin-3-amine (40 mg, 0.22 mmol) and HATU (80 mg, 0.21 mmol) in 2 mL DMF was added DIEA (104 μL, 0.6 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The solvent was removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give the title compound 73 as white solid. MS m/z 389.19 (M+1); 1H NMR 400 MHz (DMSO-d6) δ11.30 (s, 1H), 8.82 (d, 1H, J=6.4 Hz), 8.57 (d, 1H, J=2.4 Hz), 8.35 (m, 1H), 8.24 (dd, 1H, J1=6.4 Hz, J2=1.6 Hz), 8.19 (dd, 1H, J1=10.0 Hz, J2=2.8 Hz), 8.02 (m, 2H), 7.63 (m, 2H), 7.42 (d, 2H, J=9.6 Hz), 3.87 (s, 2H), 3.75 (m, 4H), 3.66 (m, 4H), 2.80 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546396B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-9726f12978e94fec9d77568ead1ddc12
Source note	uspto-grants-2013_10