Hydrochloric Acid → HCID 69482803, compound

HRID 2364409Notes

Reaction equation

HRID 2364409 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:25])=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:36][CH2:37][CH2:38][CH2:39]I.Cl>CN(C)C=O>[Cl:36][CH2:37][CH2:38][CH2:39][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:25])=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]1=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 813631-Chloro-3-iodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482803HCID 69482803, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (40 mg, 0.117 mmol) in N,N-dimethylformamide was added lithium bis(trimethylsilyl)amide (234 μL, 1.0 M in tetrahydrofuran, 0.234 mmol) dropwise. 1-Chloro-3-iodopropane (50 μL, 0.468 mmol) was added dropwise and stirred 4 hours at room temperature. The reaction mixture was acidified with cold 1 N aqueous hydrochloric acid and extracted with toluene. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided ethyl 1-(3-chloropropyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.53 (d, J=1.1 Hz, 1 H), 7.50 (s, 1 H), 7.18 (dd, J=8.6, 5.3 Hz, 2 H), 7.03 (t, J=8.6 Hz, 2 H), 4.50 (q, J=7.1 Hz, 2 H), 4.27 (t, J=7.6 Hz, 2 H), 4.13 (s, 2 H), 3.61 (t, J=5.9 Hz, 2 H), 2.09 (m, 2 H), 1.47 (t, J=7.3 Hz, 3 H); MS m/z 417 (M−H)−.

Workup

  1. extractionextracted with toluene
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-a94d6c29c1b3435aa662e6f944c02d42
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…