Phosphorus oxychloride → HCID 59811133, compound

HRID 1724836Notes

Reaction equation

HRID 1724836 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:26][O:27][CH3:28])=[N:7][C:8]2[C:13]([C:14]=1O)=[CH:12][CH:11]=[C:10]([C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=1)[N:9]=2)=[O:4].O=P(Cl)(Cl)[Cl:31]>N1C(C)=CC=CC=1C.C(Cl)(Cl)Cl>[Cl:31][C:14]1[C:13]2[C:8](=[N:9][C:10]([C:16]3[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:11][CH:12]=2)[N:7]=[C:6]([CH2:26][O:27][CH3:28])[C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178494656HCID 178494656, compound

Product 1

HCID 59811133HCID 59811133, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 79372,6-LutidineSolvent

Procedure

Dissolve 4-hydroxy-2-methoxymethyl-7-(3-trifluoromethylpyridin-2-yl)-[1,8]naphthyridine-3-carboxylic acid methyl ester (500 mg, 1.27 mmol) in a solution of POCl3 (0.4 mL), 2,6-lutidine (0.43 mL) and CHCl3 (25 mL). Heat the mixture at reflux overnight. Remove the solvent under reduced pressure. Partition the residue between CH2Cl2 and saturated NaHCO3 (aq). Extract the aqueous layer twice with CH2Cl2 (2×100 mL). Dry the combined organic extracts over Na2SO4. Remove the solvent under reduced pressure. Purify the crude product by preparatory TLC eluting with EtOAc\Hexanes (1:1) to yield the title compound.

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux overnight
  3. customRemove the solvent under reduced pressure
  4. customPartition the residue between CH2Cl2 and saturated NaHCO3 (aq)
  5. extractionExtract the aqueous layer twice with CH2Cl2 (2×100 mL)
  6. dry with materialDry the combined organic extracts over Na2SO4
  7. customRemove the solvent under reduced pressure
  8. customPurify the crude product by preparatory TLC
  9. washeluting with EtOAc\Hexanes (1:1)

Sources & evidence

ORD record
ord-be4aaa14cbf8495cb6f8c590f4313003
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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