Hydrochloric Acid → HCID 86714175, compound

HRID 1411036Notes

Reaction equation

HRID 1411036 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.F[C:35](F)(F)C(O)=O.C(N(CC)CC)C.C(OC(=O)C)(=O)C.C[O-].[Na+].Cl>C(Cl)Cl>[C: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:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:20]=[CH:21][C:22]=2[C:23]=1[OH:24])=[O:13])(=[O:5])[CH3:35]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10942334Sodium MethoxideHCID 68297412HCID 68297412, compound

Product 1

HCID 86714175HCID 86714175, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 CH2Cl2 (3 mL), triethylamine (0.25 mL, 1.79 mmol), and acetic anhydride (0.085 mL, 0.90 mmol), and the resulting mixture was stirred at r.t. for 16 h. The mixture was concentrated to dryness, and the residue was dissolved in MeOH (3.6 mL) and treated with NaOMe (3.6 mL, 1.79 mmol, 0.5 M in MeOH) for 1 h at r.t. 1 M HCl was added until pH was about 3-4, and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 37 mg of the title compound as an off-white solid. MS: (+) m/z 395.38 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo
  2. stirringthe resulting mixture was stirred at r.t. for 16 h
  3. concentrationThe mixture was concentrated to dryness
  4. dissolutionthe residue was dissolved in MeOH (3.6 mL)
  5. extractionthe mixture was extracted with EtOAc
  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-56782ed65aac4deebb037427b8c50888
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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