Hydrochloric Acid → 4-Fluoro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-ylamino)-phenyl]-2-trifluoromethyl-benzamide

HRID 1029261Notes

Reaction equation

HRID 1029261 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.Cl.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:38])[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[C:34]([F:37])([F:36])[F:35])=[CH:21][CH:20]=1.O>CCOCC>[F:33][C:30]1[CH:31]=[CH:32][C:27]([C:26]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:2]3[CH:11]=[CH:10][N:9]=[C:8]4[C:3]=3[C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[C:6](=[O:12])[NH:7]4)=[CH:24][CH:23]=2)=[O:38])=[C:28]([C:34]([F:35])([F:36])[F:37])[CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 44603462N-(4-Aminophenyl)-4-fluoro-2-trifluoromethyl-benzamideHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 581679844-Fluoro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-ylamino)-phenyl]-2-trifluoromethyl-benzamideYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 83 (135 mg, 0.59 mmol) in ether (10 mL) was added HCl (1.17 mL, 1.00 M, 1.17 mmol) in ether. The mixture was stirred for 3 h and the solvent was removed under vacuo. A suspension of this HCl salt in NMP (3 mL) was added N-(4-aminophenyl)-4-fluoro-2-(trifluoromethyl)benzamide (209 mg, 0.70 mmol). The mixture was stirred at 150° C. for 3 h. After cooling to room temperature, H2O was added. The resulting product precipitate and the solid was filtered, washed with H2O and MeOH, and dried under vacuum to provide 378 (210 mg, 73% yield) as pale solid.

Workup

  1. customthe solvent was removed under vacuo
  2. additionA suspension of this HCl salt in NMP (3 mL)
  3. stirringThe mixture was stirred at 150° C. for 3 h
  4. filtrationThe resulting product precipitate and the solid was filtered
  5. washwashed with H2O and MeOH
  6. customdried under vacuum

Sources & evidence

ORD record
ord-152b052780c44224ad1834c463c05dd5
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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