(+/-)-2-((3-((3R,4R)-4-amino-3-hydroxypiperidin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile → (+/-)-N-((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-hydroxypiperidin-4-yl)-4-methylpiperazine-1-carboxamide

HRID 921655Notes

Reaction equation

HRID 921655 reaction equation
N[C@@H]1CCN(C2C(Cl)=C(NC3N=[C:21]([NH:23][CH:24]4[CH2:26]C4)[C:20]4=[N:27][CH:28]=C(C#N)N4N=3)C=C(C#N)C=2)C[C@H]1O.[Cl:34][C:35]1[C:40]([NH:41][C:42]2[N:47]=[C:46]([NH:48][CH:49]3[CH2:51][CH2:50]3)[C:45]3=[N:52][CH:53]=[C:54]([C:55]#[N:56])[N:44]3[N:43]=2)=[CH:39][C:38]([C:57]#[N:58])=[CH:37][C:36]=1[N:59]1[CH2:64][CH2:63][C@@H:62]([NH:65][C:66](=O)[O:67]CCN(C)C)[C@H:61]([OH:74])[CH2:60]1>>[Cl:34][C:35]1[C:40]([NH:41][C:42]2[N:47]=[C:46]([NH:48][CH:49]3[CH2:51][CH2:50]3)[C:45]3=[N:52][CH:53]=[C:54]([C:55]#[N:56])[N:44]3[N:43]=2)=[CH:39][C:38]([C:57]#[N:58])=[CH:37][C:36]=1[N:59]1[CH2:64][CH2:63][C@@H:62]([NH:65][C:66]([N:23]2[CH2:21][CH2:20][N:27]([CH3:28])[CH2:26][CH2:24]2)=[O:67])[C@H:61]([OH:74])[CH2:60]1

Participants

3

Reactant 2

HCID 86708509(+/-)-2-((3-((3R,4R)-4-amino-3-hydroxypiperidin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileHCID 89922892(+/-)-2-(dimethylamino)ethyl ((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-hydroxypiperidin-4-yl)carbamate

Product 1

HCID 86708508(+/-)-N-((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-hydroxypiperidin-4-yl)-4-methylpiperazine-1-carboxamide

Procedure

The title compound was prepared from (+/−)-2-((3-((3R,4R)-4-amino-3-hydroxypiperidin-1-yl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (byproduct from Example 177), using a method analogous to that used to prepare Example 181.

Workup

  1. customto prepare Example 181

Sources & evidence

ORD record
ord-b097faf8899843ae883954de82fde82a
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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