Ammonium formate → 2-Amino-N-(4-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide

HRID 513636Notes

Reaction equation

HRID 513636 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[C:17](Cl)=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[C:21]2[O:26][CH3:27])(=[O:14])=[O:13].C([O-])=O.[NH4+]>[Pd].C(O)(=O)C.CCOC(C)=O>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[C:21]2[O:26][CH3:27])(=[O:13])=[O:14]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 681834312-Amino-N-(7-chloro-4-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide2×

Product 1

HCID 681833942-Amino-N-(4-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamideYield 101.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% palladium on carbon (82 mg) was added to a solution of 2-amino-N-(7-chloro-4-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide (Intermediate 195) (670 mg, 1.5 mmol) and ammonium formate (481 mg, 7.5 mmol) in 50% acetic acid (5 ml) and the reaction was heated under reflux for 30 min. After cooling the mixture was diluted with EtOAc (100 ml), washed sat sodium bicarbonate solution, dried (MgSO4) concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (98:2) as the eluent to give the title compound (604 mg, 100%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling the mixture
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with DCM/MeOH (98:2) as the eluent

Sources & evidence

ORD record
ord-39168b1b733d4f52a2d615d0101e16f6
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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