5-(6-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridine-2-carboxylic acid → tert-butyl (3R)-3-[(3-chloropyridin-2-yl){[5-(6-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridin-2-yl]carbonyl}amino]piperidine-1-carboxylate

HRID 588392Notes

Reaction equation

HRID 588392 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.[CH3:22][C:23]1[CH:24]=[C:25]2[N:31]=[N:30][N:29]([C:32]3[CH:33]=[CH:34][C:35]([C:38](O)=[O:39])=[N:36][CH:37]=3)[C:26]2=[N:27][CH:28]=1>>[Cl:1][C:2]1[C:3]([N:8]([C:38]([C:35]2[CH:34]=[CH:33][C:32]([N:29]3[C:26]4=[N:27][CH:28]=[C:23]([CH3:22])[CH:24]=[C:25]4[N:31]=[N:30]3)=[CH:37][N:36]=2)=[O:39])[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 1176528785-(6-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridine-2-carboxylic acidHCID 117652951(R)-tert-butyl 3-((3-chloropyridin-2-yl)amino)piperidine-1-carboxylate

Product 1

HCID 118898566tert-butyl (3R)-3-[(3-chloropyridin-2-yl){[5-(6-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridin-2-yl]carbonyl}amino]piperidine-1-carboxylateYield 43.2%

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 (3.22 g, 10.3 mmol) and Preparation 8 5-(6-methyl-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)pyridine-2-carboxylic acid (2.51 g, 9.83 mmol) to provide 2.33 g (43%) of the product as a solid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-751ca63fc8614dde97b66a62116e2873
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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