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Trifluoroacetic acid → N-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-phenyl-2-thioxoimidazolidine-1-carboxamide

HRID 84398
Notes
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Reaction equation

HRID 84398 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:43]=[C:42]([NH:44][C:45]([N:47]2[CH2:51][CH2:50][N:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:48]2=[S:58])=[O:46])[CH:41]=[CH:40][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:21]3[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH2:36][CH2:37][O:38][CH3:39])C(=O)OC(C)(C)C)=[CH:23][CH:22]=3)[S:20][C:13]=12>C(Cl)Cl>[F:8][C:9]1[CH:43]=[C:42]([NH:44][C:45]([N:47]2[CH2:51][CH2:50][N:49]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[C:48]2=[S:58])=[O:46])[CH:41]=[CH:40][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([CH2:27][NH:28][CH2:36][CH2:37][O:38][CH3:39])=[CH:25][N:26]=3)[S:20][C:13]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57919539Tert-butyl (6-(7-(2-fluoro-4-(3-phenyl-2-thioxoimidazolidine-1-carboxamido)phenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl(2-methoxyethyl)carbamate

Product 1

HCID 25270231N-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-phenyl-2-thioxoimidazolidine-1-carboxamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

TFA (1 ml, 12.98 mmol) was added to a suspension of 302 (0.093 g, 0.128 mmol) in DCM (1.000 ml) and the mixture was stirred at room temperature for 2 h. The reaction mixture was then concentrated under reduced pressure, the residue was dissolved in DCM, washed with 1N NaOH solution, water, dried over anhydrous sodium sulfate and concentrated affording title compound 303 (0.0714 g, 0.109 mmol, 85% yield) as white solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with 1N NaOH solution, water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-891155cc2a6846c691cb044621688aab
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846927B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes