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 1942810Notes

Reaction equation

HRID 1942810 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

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 6344DichloromethaneSolvent

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-9b8e1adbf50d4f2e9fdcc73333849597
Source dataset
uspto-grants-2013_03
Patent number
US08389541B2

Reaction notes

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