(R)-tert-butyl 3-((3-chloropyridin-2-yl)amino)piperidine-1-carboxylate → tert-butyl (3R)-3-[(3-chloropyridin-2-yl){[5-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridin-2-yl]carbonyl}amino]piperidine-1-carboxylate

HRID 588389Notes

Reaction equation

HRID 588389 reaction equation
[Cl:1][C:2]1[C:3]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[N:22]1[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:24]([C:31]2[CH:32]=[CH:33][C:34]([C:37](O)=[O:38])=[N:35][CH:36]=2)[N:23]=1>>[Cl:1][C:2]1[C:3]([N:8]([C:37]([C:34]2[CH:33]=[CH:32][C:31]([N:24]3[C:25]4=[N:26][CH:27]=[CH:28][CH:29]=[C:30]4[N:22]=[N:23]3)=[CH:36][N:35]=2)=[O:38])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 117652951(R)-tert-butyl 3-((3-chloropyridin-2-yl)amino)piperidine-1-carboxylateHCID 1176531005-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridine-2-carboxylic acid

Product 1

HCID 118898600tert-butyl (3R)-3-[(3-chloropyridin-2-yl){[5-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridin-2-yl]carbonyl}amino]piperidine-1-carboxylateYield 52%

Procedure

Prepared using General Procedures A and C starting from Preparation 1 tert-butyl (3R)-3-[(3-chloropyridin-2-yl)amino]piperidine-1-carboxylate (3.22 g, 10.3 mmol) and Preparation 7 5-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridine-2-carboxylic acid (2.37 g, 9.83 mmol) to provide 2.72 g (52%) of the product isolated as a solid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-078368856e5e4ccaad2c68185d841fe7
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

Loading…