Hydrochloric Acid → HCID 86714120, compound

HRID 919806Notes

Reaction equation

HRID 919806 reaction equation
C(O[C:6](=[O:32])[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]=[CH:15][C:16]2[C:17](=[O:31])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=[CH:20][C:21]=2[C:22]=1[OH:23])=[O:12])(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.[CH:47]([N:50]=C=O)([CH3:49])[CH3:48].Cl>C(Cl)Cl.CCOC(C)=O>[CH:47]([NH:50][C:6](=[O:32])[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]=[CH:15][C:16]2[C:17](=[O:31])[N:18]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=[CH:20][C:21]=2[C:22]=1[OH:23])=[O:12])([CH3:49])[CH3:48]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 68297612HCID 68297612, compound

Product 1

HCID 86714120HCID 86714120, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

{2-[(7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester (38 mg, 0.087 mmol) was dissolved in CH2Cl2 (1.5 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 (2 mL), triethylamine (0.030 mL, 0.19 mmol), and isopropyl isocyanate (0.010 mL, 0.10 mmol), and the resulting mixture was stirred at r.t. for 16 h. 1 M HCl and EtOAc were added, and the aqueous layer was extracted with additional EtOAc. The organic layers were combined and concentrated to dryness. The residue was washed with CH2Cl2, isolated by filtration, and dried to give 17 mg of the title compound as a white solid. MS: (+) m/z 424.35 (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. extractionthe aqueous layer was extracted with additional EtOAc
  4. concentrationconcentrated to dryness
  5. washThe residue was washed with CH2Cl2
  6. customisolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-22bd5c21690f418087ae49c0ebfaaa2c
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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