Trifluoroacetic acid → HCID 86714130, compound

HRID 919833Notes

Reaction equation

HRID 919833 reaction equation
C([O:5][C:6](=O)[N:7]([CH2:9][CH2:10][NH:11][C:12]([C:14]1[N:15]=[CH:16][C:17]2[C:18](=[O:32])[N:19]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:20]=[CH:21][C:22]=2[C:23]=1[OH:24])=[O:13])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.C(OCC)=O>C(Cl)Cl.C1COCC1>[CH:6]([N:7]([CH3:8])[CH2:9][CH2:10][NH:11][C:12]([C:14]1[N:15]=[CH:16][C:17]2[C:18](=[O:32])[N:19]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:20]=[CH:21][C:22]=2[C:23]=1[OH:24])=[O:13])=[O:5]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8025Ethyl formateHCID 8471TriethylamineHCID 68297219HCID 68297219, compound

Product 1

HCID 86714130HCID 86714130, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

{2-[(7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-ethyl}-methyl-carbamic acid tert-butyl ester (65 mg, 0.14 mmol) was dissolved in CH2Cl2 (2 mL). Trifluoroacetic acid (1 mL) was added, and the mixture was stirred at r.t. for 2 h. Solvent and excess TFA were removed in vacuo. To the residue were added THF (5 mL), triethylamine (0.1 mL, 0.72 mmol), and ethyl formate (5 mL), and the resulting mixture was refluxed for 4 days. Mixture was concentrated in vacuo, and the residue was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 35 mg of the title compound as a light yellow solid. MS: (+) m/z 381.34 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo
  2. temperaturethe resulting mixture was refluxed for 4 days
  3. concentrationMixture was concentrated in vacuo
  4. customthe residue was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-68c96d834ab04f7b90ea9585c1537f15
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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