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Trifluoroacetic acid → HCID 89922950, compound

HRID 921883
Notes
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Reaction equation

HRID 921883 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[C:14]([NH:15][C:16]2[N:21]=[C:20]([N:22]([CH:32]3[CH2:34][CH2:33]3)CC3C=CC(OC)=CC=3)[C:19]3=[N:35][CH:36]=[C:37]([C:38]#[N:39])[N:18]3[N:17]=2)=[CH:13][C:12]([C:40]#[N:41])=[CH:11][C:10]=1[N:42]1[CH2:47][CH2:46][N:45](C(OC(C)(C)C)=O)[CH2:44][C:43]1=[O:55].C1(OC)C=CC=CC=1>ClCCCl>[Cl:8][C:9]1[C:10]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][C:43]2=[O:55])=[CH:11][C:12]([C:40]#[N:41])=[CH:13][C:14]=1[NH:15][C:16]1[N:21]=[C:20]([NH:22][CH:32]2[CH2:34][CH2:33]2)[C:19]2=[N:35][CH:36]=[C:37]([C:38]#[N:39])[N:18]2[N:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 89923358Tert-butyl 4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 89922950HCID 89922950, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 11
1,2-Dichloroethane
Solvent

Conditions

Temperature
60 °C

Procedure

TFA (1 mL) was added to a solution of tert-butyl 4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-oxopiperazine-1-carboxylate (10 mg, 0.015 mmol) and anisole (6.53 μl, 0.060 mmol) in DCE (1 mL) and the reaction mixture was heated at 60° C. for 30 min. LC-MS indicated completion, then it was cooled and concentrated. The crude was dissolved in methanol and neutralized with 7N ammonia in methanol. After stirring for 10 min it was concentrated, purification via preparative HPLC gave the title compound as a yellow solid (3.8 mg).

Workup

  1. temperatureit was cooled
  2. concentrationconcentrated
  3. dissolutionThe crude was dissolved in methanol and neutralized with 7N ammonia in methanol
  4. concentrationwas concentrated
  5. custompurification via preparative HPLC

Sources & evidence

ORD record
ord-197c2017c08048049a4a82d505415dd2
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273057B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes