2-(Bromomethyl)benzonitrile → N-Desmethyl,N-2(2-cyanobenzyl) Alogliptin

Participants

Role	Name	HCID	Charge
Reactant	2-(Bromomethyl)benzonitrile	HCID 89599	—
Reactant	2-{6-[3(R)-Amino-piperidin-1-yl]-3-(3-cyano-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile	HCID 11775034	—
Product	N-Desmethyl,N-2(2-cyanobenzyl) Alogliptin	HCID 11487504	—

Reaction Steps

Title compound 18 was prepared by the methods used in the preparation of compound 17, except that α-bromo-o-tolunitrile was used in the place of m-cyano-benzyl bromide. 1H-NMR (400 MHz, CDCl3-CD3OD 10:1) δ 7.64 (d, J=6.8 Hz, 1H), 7.60 (d, J=7.8 Hz, 1H), 7.55 (t, J=7.8 Hz, 2H), 7.44 (t, J=7.6 Hz, 1H), 7.38 (t, J=7.5 Hz, 1H), 7.31 (t, J=7.6 Hz, 1H), 7.27 (d, J=7.8 Hz, 1H), 7.12 (d, J=7.8 Hz, 1H), 5.45 (s, 1H), 5.15-5.32 (m, 4H), 3.36-3.47 (m, 2H), 2.98 (m, 2H), 2.10 (m, 1H), 1.91 (m, 1H), 1.68 (m, 2H). MS (ES) [m+H] calc'd for C25H25N6O2, 441.2; found 441.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07781584B2
Source dataset	uspto-grants-2010_08
ORD ID	ord-f1592149c41e4797ada4ae3facfaf8b4
Source note	uspto-grants-2010_08