4-[1,2,3]Triazolo[4,5-b]pyridin-3-yl-benzoic acid → tert-butyl (3R)-3-(4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-N-(3-chloropyridin-2-yl)benzamido)piperidine-1-carboxylate

HRID 588397Notes

Reaction equation

HRID 588397 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:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=2)[N:23]=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:35]([N:8]([C@@H:9]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]3)[C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)=[O:36])=[CH:38][CH:39]=2)[N:23]=1

Participants

3

Reactant 2

HCID 124454884-[1,2,3]Triazolo[4,5-b]pyridin-3-yl-benzoic acidHCID 117652951(R)-tert-butyl 3-((3-chloropyridin-2-yl)amino)piperidine-1-carboxylate

Product 1

HCID 118898565tert-butyl (3R)-3-(4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-N-(3-chloropyridin-2-yl)benzamido)piperidine-1-carboxylateYield 79%

Procedure

Prepared according to General Procedure A and C starting from Preparation 1 tert-butyl (3R)-3-[(3-chloropyridin-2-yl)amino]piperidine-1-carboxylate (26.7 g, 85.5 mmol) and Preparation 5 4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)benzoic acid (20.1 g, 83.5 mmol) to provide 35.2 g (79%) of the product as a solid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8492152026f445d2adeedf62dad74756
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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