Trifluoroacetic acid → HCID 86714133, compound

HRID 919855Notes

Reaction equation

HRID 919855 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[C:28]([OH:51])=[C:29]2[C:34](=[CH:35][N:36]=1)[N:33]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32](=[O:44])[C:31]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[CH:30]2)=O>C(Cl)Cl>[CH3:14][S:11]([NH:10][CH2:9][CH2:8][NH:7][C:6]([C:27]1[C:28]([OH:51])=[C:29]2[C:34](=[CH:35][N:36]=1)[N:33]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32](=[O:44])[C:31]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[CH:30]2)=[O:15])(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 47454467tert-Butyl {2-[(methanesulfonyl)amino]ethyl}carbamateHCID 682973581-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

Product 1

HCID 86714133HCID 86714133, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Methanesulfonylamino-ethyl)-carbamic acid tert-butyl ester (94 mg, 0.38 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 (3 mL). NaOMe was added with vigorous stirring until pH was about 8. The resulting mixture was transferred to a microwave vial containing 1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (38 mg, 0.098 mmol), and the mixture was heated at 140° C. for 6 h in a microwave reactor. The solvent was evaporated, and the residue was partitioned between EtOAc and 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 16 mg of the title compound. MS: (+) m/z 493.32 (M+1).

Workup

  1. customSolvent and excess TFA were removed by evaporation
  2. additionNaOMe was added
  3. stirringwith vigorous stirring until pH was about 8
  4. temperaturethe mixture was heated at 140° C. for 6 h in a microwave reactor
  5. customThe solvent was evaporated
  6. customthe residue was partitioned between EtOAc and 0.1 M HCl
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2ec2533a78134317a5a5f7bca8d61532
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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