4-Methoxybenzylamine → HCID 67481371, compound

HRID 472647Notes

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

Participants

Reactant 2

HCID 754524-Methoxybenzylamine

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

Product 1

HCID 67481371HCID 67481371, compound

Procedure

(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(4-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 4-methoxy-benzenemethanamine, (1.26 mL, 9.72 mmol) in a manner analogous to Example 2d. Product isolated as an off-white solid, (1.51 g. 61%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.06 (d, J=6.90 Hz, 1H), 7.31 (d, J=8.2 Hz, 2H), 7.19 (m, 1H), 6.94 (t, J=14.4, 7.6 Hz, 1H), 6.87 (d, J=7.4 Hz, 2H), 6.42 (d, J=8.0 Hz, 1H), 4.40 (d, J=6.1 Hz, 2H), 3.71 (s, 3H). MS=289 (MH)+.

Workup

customProduct isolated as an off-white solid, (1.51 g. 61%)

Sources & evidence

ORD record: ord-32a9127ed01e4efbb4cd023dffaa11c8
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633173B2

Reaction notes

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