Diisopropylethylamine → N-(5-phenylpyridin-2-yl)-2-(4-(pyridazin-4-yl)phenyl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	5-Phenyl-2-pyridinamine	HCID 105097	—
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-(4-(Pyridazin-4-yl)phenyl)acetic acid	HCID 58447931	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(5-phenylpyridin-2-yl)-2-(4-(pyridazin-4-yl)phenyl)acetamide	HCID 46927799	—

Reaction Steps

To a mixture of 2-(4-(pyridazin-4-yl)phenyl)acetic acid 37-4 (43 mg, 0.2 mmol), 5-phenylpyridin-2-amine (41 mg, 0.24 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (117 mg, 0.3 mmol) in DMF (1 mL) was added DIEA (104 μL, 0.6 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The crude product was purified by reverse phase HPLC to give N-(5-phenylpyridin-2-yl)-2-2(4-pyridazin-4-yl)phenyl)acetamide 37 as white solid. MS m/z 367.1 (M+1); 1H NMR 400 MHz (CDCl3) δ 9.45-9.44 (m, 1H), 9.22 (dd, 1H, J1=1.2 Hz, J2=11.2 Hz), 8.44 (d, 1H, J=2.4 Hz), 8.29 (d, 1H, J=8.8 Hz), 7.92 (dd, 1H, J1=16.8 Hz, J2=2.4 Hz), 7.70-7.66 (m, 3H), 7.56-7.51 (m, 4H), 7.46-7.43 (m, 2H), 7.39-7.35 (m, 1H), 3.85 (s, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09238646B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-226265fe6fea418b9ec31e292d9a542f
Source note	uspto-grants-2016_01