HCID 178494656, compound → HCID 178494542, compound

HRID 1724833Notes

Reaction equation

HRID 1724833 reaction equation
COC([C:5]1[C:6]([CH2:26][O:27][CH3:28])=[N:7][C:8]2[C:13]([C:14]=1[OH:15])=[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>Cl>[CH3:28][O:27][CH2:26][C:6]1[CH:5]=[C:14]([OH:15])[C:13]2[C:8](=[N:9][C:10]([C:16]3[C:21]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:11][CH:12]=2)[N:7]=1

Participants

3

Reactant 1

HCID 178494656HCID 178494656, compound

Product 1

HCID 178494542HCID 178494542, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

4-Hydroxy-2-methoxymethyl-7-(3-trifluoromethyl-pyridin-2-yl)-[1,8]napthyridine-3-carboxylic acid methyl ester (200 mg, 0.508 mmol) is dissolved in 12 M HCl (20 mL) and heated at 110° C. for 6 hours. The reaction mixture is poured onto ice (100 g) and extracted with CH2Cl2 (4×150 mL). The combined organic extracts are dried over Na2SO4 and the solvent removed under reduced pressure. The crude product is purified by silica gel preparatory TLC eluting with hexanes/acetone (3:1) yielding the title compound as a white solid.

Workup

  1. additionThe reaction mixture is poured onto ice (100 g)
  2. extractionextracted with CH2Cl2 (4×150 mL)
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. customthe solvent removed under reduced pressure
  5. customThe crude product is purified by silica gel preparatory TLC
  6. washeluting with hexanes/acetone (3:1)

Sources & evidence

ORD record
ord-57831156b667466590319fa869e6e4c7
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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