Acetic Anhydride → HCID 69481486, compound

HRID 2364485Notes

Reaction equation

HRID 2364485 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:39])=[C:14]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:15](=[O:33])[N:16]3[CH2:19][CH2:20][N:21]([CH3:32])[C:22]([O:24]CC3C=CC=CC=3)=O)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:40](N(C(C)C)CC)(C)C.C(OC(=O)C)(=O)C>C(Cl)Cl.[Pd]>[C:22]([N:21]([CH3:32])[CH2:20][CH2:19][N:16]1[C:17]2[C:12](=[N:11][CH:10]=[C:9]([CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:18]=2)[C:13]([OH:39])=[C:14]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:15]1=[O:33])(=[O:24])[CH3:40]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 69482645HCID 69482645, compound

Product 1

HCID 69481486HCID 69481486, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(methyl {[(phenylmethyl)oxy]carbonyl}amino)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.023 g, 0.043 mmol) in CH2Cl2 (1.5 mL) was combined with diisopropylethylamine (0.0038 mL, 0.22 mmol), acetic anhydride (0.021 mL, 0.22 mmol) and Pd/C (0.012 g, 10% w/w). The resulting suspension was flushed with nitrogen and evacuated several times the charged with hydrogen under a balloon and stirred at ambient temperature overnight. The reaction mixture was filtered, washed with CH2Cl2, and concentrated in vacuo. The residue was dissolved in CH2Cl2, washed with 1N NaHSO4, and brine, concentrated the organics to afford the title compound as an oil: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (d, J=6.59 Hz, 3 H), 1.86 (s, 3 H), 2.94 (s, 3 H), 3.50 (t, J=6.86 Hz, 2 H), 4.18 (s, 2 H), 4.28 (q, J=6.83 Hz, 4 H), 7.12 (t, J=8.69 Hz, 2 H), 7.35-7.40 (m, 2 H), 8.02 (d, J=6.40 Hz, 1 H), 8.47 (s, 1 H); ES+ MS: 442 (M+H+).

Workup

  1. customThe resulting suspension was flushed with nitrogen
  2. customevacuated several times the
  3. additioncharged with hydrogen under a balloon
  4. filtrationThe reaction mixture was filtered
  5. washwashed with CH2Cl2
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in CH2Cl2
  8. washwashed with 1N NaHSO4, and brine
  9. concentrationconcentrated the organics

Sources & evidence

ORD record
ord-29293d07205a4ae6bd496efa629fb22f
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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