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

HRID 472655Notes

Reaction equation

HRID 472655 reaction equation
Cl[C:2]1[N:20]=[C:5]2[C:6]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[NH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1>>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][NH:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[N:20]=2)[CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 100093-AminopyridineHCID 67481427(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methoxy-benzyl)-amine

Product 1

HCID 59612460N(8)-(3-Methoxy-benzyl)-N(2)-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

N(8)-(3-Methoxy-benzyl)-N(2)-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methoxy-benzyl)-amine (99.9 mg, 0.346 mmol) and 3-aminopyridine (36.47 mg, 0.3875 mmol) in a manner analogous to Example 2d. Product isolated as an off-white foam (6.22 mg, 5%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.65 (s, 1H), 8.89 (s, 1H), 8.22 (d, J=8.6 Hz, 1H), 8.08 (m, 1H), 7.97 (d, J=6.4 Hz, 1H), 7.32-7.20 (m, 2H), 6.97 (s, 2H), 6.82-6.72 (m, 2H), 6.62 (m, 1H), 6.32 (d, J=8.1 Hz, 1H), 4.50 (d, J=6.1 Hz, 2H), 3.72 (s, 3H). MS=347 (MH)+.

Sources & evidence

ORD record
ord-eb26025aa5544a0d9f3d49e7618863fa
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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