Water → HCID 59811153, compound

HRID 1724838Notes

Reaction equation

HRID 1724838 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[N:15][C:16]([C:20]4[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=4)=[CH:17][CH:18]=3)[N:13]=[C:12]([CH2:30][O:31][CH3:32])[C:11]=2[C:33]([O:35]C)=[O:34])=[CH:5][CH:4]=1.O[Li].O.C1COCC1.O>C(O)(=O)C>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[N:15][C:16]([C:20]4[C:25]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=4)=[CH:17][CH:18]=3)[N:13]=[C:12]([CH2:30][O:31][CH3:32])[C:11]=2[C:33]([OH:35])=[O:34])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59811134HCID 59811134, compound

Product 1

HCID 59811153HCID 59811153, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Stir a solution of methyl 4-[(4-trifluoromethylphenyl)amino]-7-(3-trifluoromethylpyridin-2-yl)-2-methoxymethyl-[1,8]naphthyridine-3-carboxylate (114 mg, 0.212 mmol), LiOH.H2O (45.0 mg, 1.06 mmol), THF (2 mL) and water (0.1 mL) for 18 hours at room temperature. Add water (20 mL) and acidify with acetic acid. Extract the solution with EtOAc (3×25 mL). Wash the combined organic extracts with brine and dry over Na2SO4. Remove the solvent under reduced pressure to yield the title compound. MS 523.18 (M+1). 1H NMR δ (CDCl3) 11.50 (1H, br s), 8.89 (1H, s), 8.19 (2H, d), 7.88 (1H, dd), 7.67 (2H, m), 7.59 (1H, dd), 7.51 (2H, d), 7.22 (1H, br s), 5.30 (2H, s), 3.65 (3H, s).

Workup

  1. extractionExtract the solution with EtOAc (3×25 mL)
  2. washWash the combined organic extracts with brine
  3. dry with materialdry over Na2SO4
  4. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-a35ed46437be431aa522a190321e87bd
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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