Aniline → Methyl ((3S,4S)-3-((tert-butyldimethylsilyl)oxy)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)piperidin-4-yl)carbamate

HRID 921648Notes

Reaction equation

HRID 921648 reaction equation
[NH2:1][C:2]1[C:3]([Cl:29])=[C:4]([N:10]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17](=[O:20])[O:18][CH3:19])[C@@H:12]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:11]2)[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.NC1C=CC=CC=1.[CH:37]1([N:40]([CH2:56][C:57]2[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][CH:58]=2)[C:41]2[C:46]3=[N:47][CH:48]=[C:49]([C:50]#[N:51])[N:45]3[N:44]=[C:43](S(C)(=O)=O)[N:42]=2)[CH2:39][CH2:38]1>>[Si:22]([O:21][C@@H:12]1[C@@H:13]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH2:14][CH2:15][N:10]([C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([NH:1][C:43]3[N:42]=[C:41]([N:40]([CH:37]4[CH2:39][CH2:38]4)[CH2:56][C:57]4[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][CH:58]=4)[C:46]4=[N:47][CH:48]=[C:49]([C:50]#[N:51])[N:45]4[N:44]=3)[C:3]=2[Cl:29])[CH2:11]1)([C:25]([CH3:26])([CH3:28])[CH3:27])([CH3:23])[CH3:24]

Participants

4

Reactant 3

HCID 6115AnilineHCID 86708519HCID 86708519, compoundHCID 89919054Methyl((3S,4S)-1-(3-amino-2-chloro-5-cyanophenyl)-3-((tert-butyldimethylsilyl)oxy)piperidin-4-yl)carbamate

Product 1

HCID 131732380Methyl ((3S,4S)-3-((tert-butyldimethylsilyl)oxy)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)piperidin-4-yl)carbamate

Procedure

methyl ((3S,4S)-3-((tert-butyldimethylsilyl)oxy)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)piperidin-4-yl)carbamate was prepared starting from methyl ((3S,4S)-1-(3-amino-2-chloro-5-cyanophenyl)-3-((tert-butyldimethylsilyl)oxy) piperidin-4-yl)carbamate (127 mg, 0.289 mmol) according to general procedure for the coupling of aniline to 4-(cyclopropyl(4-methoxybenzyl)amino)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile, method described for Example 7. Methyl ((3S,4S)-3-((tert-butyldimethylsilyl)oxy)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)piperidin-4-yl)carbamate (180 mg) was obtained as a white solid.

Workup

  1. custommethyl ((3S,4S)-3-((tert-butyldimethylsilyl)oxy)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)piperidin-4-yl)carbamate was prepared

Sources & evidence

ORD record
ord-91d73e75a4994cef995ad238897aef6a
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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