3-Aminopyridine → N(8)-(2-Methoxy-benzyl)-N(2)-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

HRID 472657

Reaction equation

HRID 472657 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[C:9]1[N:27]=[C:12]2[C:13]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH3:26])=[CH:14][CH:15]=[CH:16][N:11]2[N:10]=1>>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:13]1[C:12]2[N:11]([N:10]=[C:9]([NH:1][C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)[N:27]=2)[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 100093-AminopyridineHCID 67479414(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methoxy-benzyl)-amine

Product 1

HCID 59612503N(8)-(2-Methoxy-benzyl)-N(2)-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

N(8)-(2-Methoxy-benzyl)-N(2)-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from 3-aminopyridine (36.47 mg, 0.3875 mmol) and (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(2-methoxy-benzyl)-amine (99.9 mg, 0.346 mmol) in a manner analogous to Example 2d. Product isolated as an off-white foam (19.21 mg, 16%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.68 (s, 1H), 8.88 (s, 1H), 8.21 (d, J=8.6 Hz, 1H), 8.09 (s, 1H), 7.99 (d, J=7.5 Hz, 1H), 7.33-7.20 (m, 3H), 7.03 (d, J=8.6 Hz, 1H), 6.87 (t, J=15.2, 8.1 Hz, 1H), 6.77 (t, J=13.5, 6.6 Hz, 1H), 6.31 (m, 2H), 4.47 (d, J=5.8 Hz, 2H), 3.87 (s, 3H). MS=347 (MH)+.

Sources & evidence

ORD record
ord-0138c601e80b4c58b0d108b10993e034
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Linked notes

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