Trifluoroacetic acid → 3-(3-Aminophenoxy)-5-[(2-fluoro-4-iodophenyl)amino]isonicotinamide

HRID 2167223Notes

Reaction equation

HRID 2167223 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])=[CH:8][N:7]=[CH:6][C:5]=1[O:19][C:20]1[CH:21]=[C:22]([NH:26]C(=O)OC(C)(C)C)[CH:23]=[CH:24][CH:25]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[O:19][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])[C:4]=1[C:1]([NH2:2])=[O:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 56970468Tert-butyl [3-({4-carbamoyl-5-[(2-fluoro-4-iodophenyl)amino]pyridin-3-yl}oxy)phenyl]carbamate

Product 1

HCID 569704693-(3-Aminophenoxy)-5-[(2-fluoro-4-iodophenyl)amino]isonicotinamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

840 mg of tert-butyl [3-({4-carbamoyl-5-[(2-fluoro-4-iodophenyl)amino]pyridin-3-yl}oxy)phenyl]carbamate (1.488 mmol, 1 eq.) were dissolved in 8 mL dichloromethane under a nitrogen atmosphere. Then 1.6 ml of TFA were added and the brownish solution was stirred at room temperature for 18 hours. Then 4 ml of saturated aqueouse NaHCO3 solution was added and the mixture was stirred for 4 hours while a suspension was forming, that was filtered off. Drying of the precipitate in vacuo yielded 615 mg of the analytically pure target compound (1.488 mmol, 87% yield) as a yellowish solid.

Workup

  1. stirringthe mixture was stirred for 4 hours while a suspension
  2. customwas forming
  3. filtrationthat was filtered off
  4. customDrying of the precipitate in vacuo

Sources & evidence

ORD record
ord-1eeaa369d3a440b5b570021e628bf8c1
Source dataset
uspto-grants-2015_06
Patent number
US09045429B2

Reaction notes

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