Trifluoroacetic acid → HCID 86714126, compound

HRID 919818Notes

Reaction equation

HRID 919818 reaction equation
C(O[C:6](=[O:15])[NH:7][CH2:8][CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])(C)(C)C.FC(F)(F)C(O)=O.COC([C:27]1[N:28]=[CH:29][C:30]2[C:31](=[O:45])[N:32]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:33]=[CH:34][C:35]=2[C:36]=1[OH:37])=O>C(Cl)Cl.CCOC(C)=O>[CH3:14][S:11]([NH:10][CH2:9][CH2:8][NH:7][C:6]([C:27]1[N:28]=[CH:29][C:30]2[C:31](=[O:45])[N:32]([CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:33]=[CH:34][C:35]=2[C:36]=1[OH:37])=[O:15])(=[O:12])=[O:13]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 47454467tert-Butyl {2-[(methanesulfonyl)amino]ethyl}carbamateHCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 86714126HCID 86714126, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Methanesulfonylamino-ethyl)-carbamic acid tert-butyl ester (77 mg, 0.32 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 by evaporation, and the residue was taken up in EtOH (2 mL). NaOMe was added with vigorous stirring until pH about 8. The resulting cloudy solution was transferred to a microwave vial containing 7-benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (25 mg, 0.081 mmol), and the mixture was heated at 140° C. for 6 h in a microwave reactor. The mixture was diluted with EtOAc and washed with 0.1 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 20 mg of the title compound as an off-white solid. MS: (+) m/z 417.30 (M+1).

Workup

  1. customSolvent and excess TFA were removed by evaporation
  2. additionNaOMe was added
  3. stirringwith vigorous stirring until pH about 8
  4. temperaturethe mixture was heated at 140° C. for 6 h in a microwave reactor
  5. washwashed with 0.1 M HCl
  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-d053dd8d455f4d92a3c443a29898fbe5
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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