3-Methoxybenzylamine → (2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methoxy-benzyl)-amine

HRID 472646Notes

Reaction equation

HRID 472646 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([Cl:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][NH2:18]>>[Cl:11][C:9]1[N:10]=[C:3]2[C:2]([NH:18][CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH3:12])[CH:15]=3)=[CH:7][CH:6]=[CH:5][N:4]2[N:8]=1

Participants

3

Reactant 2

HCID 211563-MethoxybenzylamineHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 1

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

Procedure

(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methoxy-benzyl)-amine was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (2.00 g, 8.60 mmol), and 3-methoxy-benzylamine (1.26 mL, 9.72 mmol) in a manner analogous to Example 2d. Product was isolated as an off-white solid, (1.90 g. 77%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.08 (d, J=6.4 Hz, 1H), 7.24 (m, 2H), 6.96 (s, 3H), 6.79 (d, J=8.0 Hz, 1H), 6.41 (d, J=8.0 Hz, 1H), 4.44 (d, J=5.9 Hz, 2H), 3.71 (s, 3H).

Workup

  1. customProduct was isolated as an off-white solid, (1.90 g. 77%)

Sources & evidence

ORD record
ord-ceca0328a84c4e37b4523404fd128e9f
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

Loading…