1-(5-Aminopyridin-2-yl)azetidin-3-ol → N-[6-(3-Hydroxyazetidin-1-yl)pyridin-3-yl]-1-(3-fluorobenzyl)-5-trifluoromethyl-1H-indole-2-carboxamide

HRID 2041950Notes

Reaction equation

HRID 2041950 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[C:7]([C:20]([OH:22])=O)=[CH:6]2.[OH:25][CH:26]1[CH2:29][N:28]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][N:31]=2)[CH2:27]1>>[OH:25][CH:26]1[CH2:29][N:28]([C:30]2[N:31]=[CH:32][C:33]([NH:36][C:20]([C:7]3[N:8]([CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=4)[C:9]4[C:5]([CH:6]=3)=[CH:4][C:3]([C:2]([F:23])([F:1])[F:24])=[CH:11][CH:10]=4)=[O:22])=[CH:34][CH:35]=2)[CH2:27]1

Participants

3

Reactant 2

HCID 574315251-(5-Aminopyridin-2-yl)azetidin-3-olHCID 574315325-trifluoromethyl-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 57431500N-[6-(3-Hydroxyazetidin-1-yl)pyridin-3-yl]-1-(3-fluorobenzyl)-5-trifluoromethyl-1H-indole-2-carboxamide

Procedure

The process is carried out according to the method described in example 2, using 5-trifluoromethyl-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid (WO 2006/072736) and 2-(3-hydroxyazetidin-1-yl)-5-aminopyridine, prepared in step 10.2 of example 10 (Compound Ve).

Workup

  1. customprepared in step 10.2 of example 10 (Compound Ve)

Sources & evidence

ORD record
ord-9c4d905f22ae43b7967c9504395029ca
Source dataset
uspto-grants-2013_11
Patent number
US08586573B2

Reaction notes

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