Hydrochloric Acid → HCID 59811153, compound

HRID 2113628Notes

Reaction equation

HRID 2113628 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH2:36][O:37][CH3:38])=[N:7][C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)=[CH:12][CH:11]=[C:10]([C:26]1[C:31]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:29]=[CH:28][N:27]=1)[N:9]=2)=[O:4].O[Li].O.Cl>CO.O>[CH3:38][O:37][CH2:36][C:6]1[C:5]([C:3]([OH:4])=[O:2])=[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=2)[C:13]2[C:8](=[N:9][C:10]([C:26]3[C:31]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:11][CH:12]=2)[N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59811134HCID 59811134, compound

Product 1

HCID 59811153HCID 59811153, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Dissolve 2-methoxymethyl-4-(4-trifluoromethyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-[1,8]napthyridine-3-carboxylic acid methyl ester (150 mg, 0.279 mmol) in a solution of MeOH (6 mL), H2O (2 mL), and LiOH.H2O (58.6 mg, 1.40 mmol). Stir the mixture overnight at room temperature. Add water (30 mL) and acidify the mixture with 3 N HCl. Extract with CH2Cl2 (2×40 mL). Dry the combined organic extracts over Na2SO4. Remove the solvent under reduced pressure and chromatograph the crude product on silica gel eluting with CH2Cl2/MeOH/AcOH (95:5:1) to yield the title compound. MS 523.18 (M+1).

Workup

  1. extractionExtract with CH2Cl2 (2×40 mL)
  2. dry with materialDry the combined organic extracts over Na2SO4
  3. customRemove the solvent under reduced pressure and chromatograph the crude product on silica gel eluting with CH2Cl2/MeOH/AcOH (95:5:1)

Sources & evidence

ORD record
ord-e462d2fa0060406f8581f677df674ca5
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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