Trifluoroacetic acid → HCID 86714124, compound

HRID 919815Notes

Reaction equation

HRID 919815 reaction equation
C(O[C:6](=[O:33])[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.[F:34][C:35]([F:40])([F:39])C(O)=O.C(N(CC)CC)C.FC(F)(F)C(OCC)=O>C(Cl)Cl.C1COCC1>[CH3:8][N:7]([C:6](=[O:33])[C:35]([F:40])([F:39])[F:34])[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]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 68297219HCID 68297219, compound

Product 1

HCID 86714124HCID 86714124, compound

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 (25 mg, 0.055 mmol) was dissolved in CH2Cl2 (1.5 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 (3 mL), triethylamine (0.040 mL, 0.28 mmol), and ethyl trifluoroacetate (2 mL), and the resulting mixture was refluxed for 16 h. The mixture was concentrated to dryness, and the residue was dissolved in EtOAc and washed with 1 M HCl. The organic layers were dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 5.4 mg of the title compound as a white solid. MS: (+) m/z 449.29 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo
  2. temperaturethe resulting mixture was refluxed for 16 h
  3. concentrationThe mixture was concentrated to dryness
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with 1 M HCl
  6. dry with materialThe organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6a6e4b8fc08046659738f76f1b76c421
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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