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

HRID 505896Notes

Reaction equation

HRID 505896 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]([CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17]#[N:18])[C:12](=[O:23])[N:11]([CH2:24]C3C=CC=C(C#N)C=3)[C:10](=[O:33])[CH:9]=2)[CH2:3]1.BrC[C:36]1[C:37]([C:42]#[N:43])=[CH:38][CH:39]=[CH:40][CH:41]=1>>[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]([CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17]#[N:18])[C:12](=[O:23])[N:11]([CH2:24][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:42]#[N:43])[C:10](=[O:33])[CH:9]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 895992-(Bromomethyl)benzonitrileHCID 117750342-{6-[3(R)-Amino-piperidin-1-yl]-3-(3-cyano-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile

Product 1

HCID 11487504N-Desmethyl,N-2(2-cyanobenzyl) Alogliptin

Procedure

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.

Sources & evidence

ORD record
ord-f1592149c41e4797ada4ae3facfaf8b4
Source dataset
uspto-grants-2010_08
Patent number
US07781584B2

Reaction notes

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