5-(Piperidin-4-YL)-1H-indazole → 4-(1-(4-Cyclobutyl-2-methyl-5-(5-methyl-4H-1,2,4-triazol-3-yl)benzoyl)-3-fluoroazetidin-3-yl)benzonitrile

HRID 1487948Notes

Reaction equation

HRID 1487948 reaction equation
[CH:1]1([C:5]2[C:13]([C:14]3[NH:18][C:17]([CH3:19])=[N:16][N:15]=3)=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([CH3:20])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.C1(C2C(C(=O)NC)=CC(C(O)=O)=C(C)C=2)CCC1.Cl.[F:40][C:41]1([C:45]2[CH:52]=[CH:51][C:48]([C:49]#[N:50])=[CH:47][CH:46]=2)[CH2:44][NH:43][CH2:42]1.N1CCC(C2C=C3C(=CC=2)NN=C3)CC1>>[CH:1]1([C:5]2[C:13]([C:14]3[NH:18][C:17]([CH3:19])=[N:16][N:15]=3)=[CH:12][C:8]([C:9]([N:43]3[CH2:42][C:41]([C:45]4[CH:46]=[CH:47][C:48]([C:49]#[N:50])=[CH:51][CH:52]=4)([F:40])[CH2:44]3)=[O:11])=[C:7]([CH3:20])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 4

HCID 497608595-(Piperidin-4-YL)-1H-indazoleHCID 900213344-(3-Fluoroazetidin-3-yl)benzonitrile hydrochloride2×HCID 900220514-Cyclobutyl-2-methyl-5-(methylcarbamoyl)benzoic acidHCID 178433965HCID 178433965, compound2×

Product 1

HCID 1784339644-(1-(4-Cyclobutyl-2-methyl-5-(5-methyl-4H-1,2,4-triazol-3-yl)benzoyl)-3-fluoroazetidin-3-yl)benzonitrile

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 62, except 4-cyclobutyl-2-methyl-5-(5-methyl-4H-1,2,4-triazol-3-yl)benzoic acid (compound 78.4) was used in place of 4-cyclobutyl-2-methyl-5-(methylcarbamoyl)benzoic acid (compound 62.3) and 4-(3-fluoroazetidin-3-yl)benzonitrile hydrochloride (compound 43.4) was used in place of 5-(piperidin-4-yl)-1H-indazole (compound 62.5). m/z (ES+) 430 (M+H)+.

Sources & evidence

ORD record
ord-bdfae158759d4788bd4efca37f8abb66
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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