Trifluoroacetic acid → HCID 86714131, compound

HRID 919834Notes

Reaction equation

HRID 919834 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.F[C:35](F)(F)C(O)=O.C(N(CC)CC)C.C(OC(=O)C)(=O)C>C(Cl)Cl>[C: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])[CH3:35]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68297219HCID 68297219, compound

Product 1

HCID 86714131HCID 86714131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

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 CH2Cl2 (3 mL), triethylamine (0.2 mL, 1.4 mmol), and acetic anhydride (0.070 mL, 0.72 mmol), and the resulting mixture was stirred for 16 h. The mixture was diluted with CH2Cl2 (50 mL) and washed with 0.1 M HCl, saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated. The crude product was dissolved in MeOH (3 mL) and treated with 2.9 mL of 0.5 M NaOMe solution. After stirring for 1 h at r.t., 1 M HCl was added to acidify the mixture. The resulting suspension was extracted with EtOAc, and the organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 32 mg of the title compound. MS: (+) m/z 395.32 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo
  2. stirringthe resulting mixture was stirred for 16 h
  3. washwashed with 0.1 M HCl, saturated NaHCO3 and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. dissolutionThe crude product was dissolved in MeOH (3 mL)
  7. additiontreated with 2.9 mL of 0.5 M NaOMe solution
  8. stirringAfter stirring for 1 h at r.t.
  9. addition1 M HCl was added
  10. extractionThe resulting suspension was extracted with EtOAc
  11. dry with materialthe organic layer was dried over MgSO4
  12. concentrationconcentrated
  13. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-004abd7bf6c74c41baa9ea161d4d7704
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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