Benzylamine → 2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide

Participants

Role	Name	HCID	Charge
Reactant	Benzylamine	HCID 7504	—
Reactant	Diisopropylethylamine	HCID 81531	—
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 178522847	HCID 178522847	—
Reactant	HCID 178524246	HCID 178524246	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide	HCID 178522992	—

Reaction Steps

2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide was synthesized from 2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid, benzylamine, DIEA, HATU and DMF using a similar procedure as 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid 3-fluoro-benzylamide yielding 2-{4-[2-(3-chloro-phenyl)-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzoimidazole-4-carboxylic acid 4-fluoro-benzylamide. LC/MS calcd for C28H23ClFN5O2 (m/e) 515.0, obsd 516 (M+H). 1H NMR (tautomers, DMSO-d6): 13.30-13.51 (m, 1H), 11.11-11.49 (m, 1H), 9.98-10.95 (m, 1H), 9.06-9.36 (m, 1H), 7.68-8.00 (m, 2H), 6.93-7.65 (m, 11H), 6.22 (d, J=7.3 Hz, 1H), 4.47-4.74 (m, 2H), 3.59-3.85 (m, 2H), 3.05 (t, J=6.9 Hz, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181218B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-2256f5c119bd456a9be1dd178dc373f0
Source note	uspto-grants-2015_11