6-Methoxy-3-pyridinylamine → N(8)-(3-Methoxy-benzyl)-N(2)-(6-methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

HRID 472651Notes

Reaction equation

HRID 472651 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]=[CH:24][C:25]([O:28][CH3:29])=[N: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:27]=[N:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:20]=2)[CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 811216-Methoxy-3-pyridinylamineHCID 67481427(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methoxy-benzyl)-amine

Product 1

HCID 59612563N(8)-(3-Methoxy-benzyl)-N(2)-(6-methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine

Procedure

N(8)-(3-Methoxy-benzyl)-N(2)-(6-methoxy-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 5-amino-2-methoxypyridine (48.11 mg, 0.3875 mmol) in a manner analogous to Example 2d. Product was isolated as a red foam (41.48 mg, 32%). 1H NMR (400 MHz, CD3OD, δ, ppm): 8.42 (s, 1H), 8.04 (d, J=9 Hz, 1H), 7.83 (d, J=6.5 Hz, 1H), 7.24 (m, 1H), 6.98 (s, 2H), 6.83-6.71 (m, 3H), 6.40 (d, J=7.4 Hz, 1H), 4.48 (s, 2H), 3.88 (s, 3H), 3.76 (s, 3H). MS=377 (MH)+.

Sources & evidence

ORD record
ord-3b6fdd59d67c4617b052128e88d3699c
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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