Trifluoroacetic acid → HCID 60151265, compound

HRID 1410813Notes

Reaction equation

HRID 1410813 reaction equation
C(O[C:6](=[O:32])[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]=[CH:15][C:16]2[C:17](=[O:31])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=[CH:20][C:21]=2[C:22]=1[OH:23])=[O:12])(C)(C)C.[F:33][C:34]([F:39])([F:38])C(O)=O.C(N(CC)CC)C.FC(F)(F)C(OCC)=O>C(Cl)Cl.C1COCC1>[F:33][C:34]([F:39])([F:38])[C:6]([NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]=[CH:15][C:16]2[C:17](=[O:31])[N:18]([CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:19]=[CH:20][C:21]=2[C:22]=1[OH:23])=[O:12])=[O:32]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 68297612HCID 68297612, compound

Product 1

HCID 60151265HCID 60151265, 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}-carbamic acid tert-butyl ester (30 mg, 0.068 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 (0.050 mL, 0.34 mmol), and ethyl trifluoroacetate (2 mL), and the mixture was refluxed for 48 h. After cooling to r.t., the mixture was concentrated to dryness. The residue was partitioned between EtOAc and water, and pH was adjusted to about 4 with 1 M HCl. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 12 mg of the title compound as a pale yellow solid. MS: (+) m/z 435.31 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo
  2. temperaturethe mixture was refluxed for 48 h
  3. temperatureAfter cooling to r.t.
  4. concentrationthe mixture was concentrated to dryness
  5. customThe residue was partitioned between EtOAc and water, and pH
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a90d50d6c8b84f2db856e0b65646046b
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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