Trifluoroacetic acid → N-(5-(4-amino-3-chlorophenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-5-iodonicotinamide

HRID 1958187Notes

Reaction equation

HRID 1958187 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([O:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[N:19][CH:20]=[C:21]([NH:23][C:24]([C:26]3[CH:27]=[N:28][CH:29]=[C:30]([I:32])[CH:31]=3)=[O:25])[CH:22]=2)=[CH:13][C:12]=1[Cl:39])C1C=CC=CC=1.FC(F)(F)C(O)=O>>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[C:21]([NH:23][C:24](=[O:25])[C:26]3[CH:31]=[C:30]([I:32])[CH:29]=[N:28][CH:27]=3)[CH:20]=[N:19][C:18]=2[O:33][CH2:34][C:35]([F:36])([F:37])[F:38])=[CH:13][C:12]=1[Cl:39]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67282185{2-Chloro-4-[5-[(5-iodo-pyridine-3-carbonyl)-amino]-2-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-phenyl}-carbamic acid benzyl ester

Product 1

HCID 56961948N-(5-(4-amino-3-chlorophenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-5-iodonicotinamideYield 84.7%

Procedure

{2-Chloro-4-[5-[(5-iodo-pyridine-3-carbonyl)-amino]-2-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-phenyl}-carbamic acid benzyl ester (87 mg, 127 μmol) was, with cooling, combined with trifluoroacetic acid (3 mL) to give a brown solution. The reaction mixture was warmed to room temperature and stirred for 72 h. The crude reaction mixture was concentrated in vacuo, poured into 50 mL ethyl acetate and extracted with 1 M NaOH (1×25 mL). The aqueous layer was washed with ethyl acetate (1×50 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 0% to 40% EtOAc in heptane) to give the title compound (59 mg, 84%); LC-MS (UV peak area/ESI) 98.1%, 548.9795 (M+H)+.

Workup

  1. temperaturewith cooling
  2. customto give a brown solution
  3. customThe crude reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additionpoured into 50 mL ethyl acetate
  6. extractionextracted with 1 M NaOH (1×25 mL)
  7. washThe aqueous layer was washed with ethyl acetate (1×50 mL)
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by flash chromatography (silica gel, 20 g, 0% to 40% EtOAc in heptane)

Sources & evidence

ORD record
ord-b9e086049e414fe79604febcc9e3a881
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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