Trifluoroacetic acid → 1-(2-{5-Fluoro-4-[7-(2-fluoro-5-((methylamino)methyl)pyridin-4-yl)benzo[b]thiophen-2-yl]pyrimidin-2-ylamino}ethyl)-1H-imidazol-2(3H)-one

HRID 561034Notes

Reaction equation

HRID 561034 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([F:48])=[CH:21][C:22]=1[C:23]1[C:28]2[S:29][C:30]([C:32]3[C:37]([F:38])=[CH:36][N:35]=[C:34]([NH:39][CH2:40][CH2:41][N:42]4[CH:46]=[CH:45][NH:44][C:43]4=[O:47])[N:33]=3)=[CH:31][C:27]=2[CH:26]=[CH:25][CH:24]=1)C)(C)(C)C>ClCCl>[F:38][C:37]1[C:32]([C:30]2[S:29][C:28]3[C:23]([C:22]4[C:17]([CH2:16][NH:14][CH3:13])=[CH:18][N:19]=[C:20]([F:48])[CH:21]=4)=[CH:24][CH:25]=[CH:26][C:27]=3[CH:31]=2)=[N:33][C:34]([NH:39][CH2:40][CH2:41][N:42]2[CH:46]=[CH:45][NH:44][C:43]2=[O:47])=[N:35][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66998009Tert-butyl (6-fluoro-4-(2-(5-fluoro-2-(2-(2-oxo-2,3-dihydro-1H-imidazol-1-yl)ethylamino)pyrimidin-4-yl)benzo[b]thiophen-7-yl)pyridin-3-yl)methyl(methyl)carbamate

Product 1

HCID 249368451-(2-{5-Fluoro-4-[7-(2-fluoro-5-((methylamino)methyl)pyridin-4-yl)benzo[b]thiophen-2-yl]pyrimidin-2-ylamino}ethyl)-1H-imidazol-2(3H)-oneYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoro-acetic acid (1 mL) to a solution of [6-fluoro-4-(2-{5-fluoro-2-[2-(2-oxo-2,3-dihydro-imidazol-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophen-7-yl)-pyridin-3-ylmethyl]-methyl-carbamic acid tert-butyl ester (280 mg, 0.47 mmol) in dichloromethane (1 mL). Stir for 1 hour and remove solvent on a rotovap. Wash with saturated NaHCO3 and extract in dichloromethane, wash with saturated aqueous sodium chloride, dry over Na2SO4, and filter. Remove solvent on a rotovap to obtain the solid and dry under vacuum to afford the product (196 mg). MS (ES) m/z 494 [M+1]+.

Workup

  1. customremove solvent on a rotovap
  2. washWash with saturated NaHCO3
  3. extractionextract in dichloromethane
  4. washwash with saturated aqueous sodium chloride
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. customRemove solvent on a rotovap to obtain the solid
  8. customdry under vacuum

Sources & evidence

ORD record
ord-e2bb3ff2afbc46959046ce8a961bcebf
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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