Trifluoroacetic acid → HCID 86714174, compound

HRID 920037Notes

Reaction equation

HRID 920037 reaction equation
C([O:5][C:6](=O)[NH:7][CH2:8][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:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:20]=[CH:21][C:22]=2[C:23]=1[OH:24])=[O:13])(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.C(OCC)=O>C(Cl)Cl.C1COCC1>[CH:6]([NH:7][CH2:8][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 68297412HCID 68297412, compound

Product 1

HCID 86714174HCID 86714174, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

{3-[(7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-propyl}-carbamic acid tert-butyl ester (81 mg, 0.18 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 (0.12 mL, 0.90 mmol), and ethyl formate (5 mL), and the resulting mixture was refluxed for 4 days. The mixture was concentrated to dryness, and the residue was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 46 mg of the title compound as an off-white solid. MS: (+) m/z 381.37 (M+1).

Workup

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

Sources & evidence

ORD record
ord-1a326c4b9dbb45efa7eb3db8b5b887c9
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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