3-(Aminomethyl)benzeneboronic acid, N-BOC protected → [3-(2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-benzyl]-carbamic acid tert-butyl ester

HRID 451484Notes

Reaction equation

HRID 451484 reaction equation
Br[C:2]1[C:3]2[N:4]([N:9]=[C:10]([NH2:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18](=[O:19])[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:2]2[C:3]3[N:4]([N:9]=[C:10]([NH2:12])[N:11]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH:23]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 36846863-(Aminomethyl)benzeneboronic acid, N-BOC protectedHCID 214643388-Bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 67335256[3-(2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-benzyl]-carbamic acid tert-butyl ester

Procedure

Prepared in analogy to example 160b, starting from 8-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine and 3-((tert-butoxycarbonylamino)methyl)phenylboronic acid. The title compound was obtained as an off-white solid (yield: 99%) after precipitation from diethyl ether. MS ISP (m/e): 354.4 (80) [(M+H)+], 298.4 (100), 237.2 (99).

Workup

  1. customPrepared in analogy to example 160b

Sources & evidence

ORD record
ord-1f85a5d8ff074d9d9653eaea70fe8924
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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