Sodium Iodide → HCID 22258978, compound

HRID 2115729Notes

Reaction equation

HRID 2115729 reaction equation
[O:1](P(CC(OCC)=O)(OC1C=CC=CC=1)=O)[C:2]1C=CC=C[CH:3]=1.N12CCCN=C1CCCCC2.[Na+].[I-].[NH2:36][C:37]1[C:42]([CH:43]=O)=[C:41]([CH:45]2[CH2:50][CH2:49][CH2:48][N:47]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:46]2)[CH:40]=[C:39]([C:58]2[C:63]([O:64][CH2:65][C:66]3[CH:71]=[CH:70][C:69]([O:72][CH3:73])=[CH:68][CH:67]=3)=[CH:62][CH:61]=[CH:60][C:59]=2[O:74][CH2:75][CH:76]2[CH2:78][CH2:77]2)[N:38]=1>C1COCC1>[CH:76]1([CH2:75][O:74][C:59]2[CH:60]=[CH:61][CH:62]=[C:63]([O:64][CH2:65][C:66]3[CH:71]=[CH:70][C:69]([O:72][CH3:73])=[CH:68][CH:67]=3)[C:58]=2[C:39]2[CH:40]=[C:41]([CH:45]3[CH2:50][CH2:49][CH2:48][N:47]([C:51]([O:53][C:54]([CH3:56])([CH3:55])[CH3:57])=[O:52])[CH2:46]3)[C:42]3[CH:43]=[CH:3][C:2](=[O:1])[NH:36][C:37]=3[N:38]=2)[CH2:78][CH2:77]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11056297Ethyl DiphenylphosphonoacetateHCID 22258763HCID 22258763, compound

Product 1

HCID 22258978HCID 22258978, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl (diphenoxyphosphoryl)acetate (1.090 g, 3.403 mmol) in THF (15 mL) were added 1,8-diazabicyclo[5,4,0]undec-7-ene (0.520 g, 3.403 mmol) and NaI (0.510 g, 3.403 mmol) followed by a solution of tert-butyl 3-(2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]-phenyl}-3-formyl-4-pyridinyl)-1-piperidinecarboxylate (1.000 g, 1.701 mmol), obtained in the step (1) of Example 25-2, in THF (5 mL). The mixture was stirred at 0° C. for 1.5 hrs and quenched with saturated aqueous NaHCO3 solution. The mixture was extracted with ethyl acetate, and the extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3:2 to 1:2) to give tert-butyl 3-(2-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-7-oxo-7,8-dihydro-1,8-naphthyridin-4-yl)-1-piperidinecarboxylate as an amorphous solid (0.276 g, 27%).

Workup

  1. customquenched with saturated aqueous NaHCO3 solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3:2 to 1:2)

Sources & evidence

ORD record
ord-d97d89be065f4e569d15162d64223d32
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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