HCID 86708519, compound → (+/-)-N-((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl amino) imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-4-hydroxypiperidin-3-yl)acetamide

HRID 921658Notes

Reaction equation

HRID 921658 reaction equation
[CH:1]1([N:4](CC2C=CC(OC)=CC=2)[C:5]2[C:10]3=[N:11][CH:12]=[C:13]([C:14]#[N:15])[N:9]3[N:8]=[C:7](S(C)(=O)=O)[N:6]=2)[CH2:3][CH2:2]1.[NH2:29][C:30]1[C:31]([Cl:56])=[C:32]([N:38]2[CH2:43][CH2:42][C@@H:41]([O:44][Si](C(C)(C)C)(C)C)[C@H:40]([NH:52][C:53](=[O:55])[CH3:54])[CH2:39]2)[CH:33]=[C:34]([C:36]#[N:37])[CH:35]=1>>[Cl:56][C:31]1[C:30]([NH:29][C:7]2[N:6]=[C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)[C:10]3=[N:11][CH:12]=[C:13]([C:14]#[N:15])[N:9]3[N:8]=2)=[CH:35][C:34]([C:36]#[N:37])=[CH:33][C:32]=1[N:38]1[CH2:43][CH2:42][C@@H:41]([OH:44])[C@H:40]([NH:52][C:53](=[O:55])[CH3:54])[CH2:39]1

Participants

3

Reactant 2

HCID 86708519HCID 86708519, compound2×HCID 86708520(+/-)-N-((3R,4R)-1-(3-amino-2-chloro-5-cyanophenyl)-4-((tert-butyldimethylsilyl)oxy) piperidin-3-yl)acetamide

Product 1

HCID 86708518(+/-)-N-((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl amino) imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-4-hydroxypiperidin-3-yl)acetamide

Procedure

(+/−)-N-((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl amino) imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-4-hydroxypiperidin-3-yl)acetamide was prepared starting from 4-(cyclopropyl(4-methoxybenzyl)amino)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Intermediate 2) and (+/−)-N-((3R,4R)-1-(3-amino-2-chloro-5-cyanophenyl)-4-((tert-butyldimethylsilyl)oxy) piperidin-3-yl)acetamide using a method analogous to that used to prepare Example 171.

Workup

  1. customto prepare Example 171

Sources & evidence

ORD record
ord-fb6b8c84028949a8b4826c7f893e92e2
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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