Hydrochloric Acid → HCID 67209398, compound

HRID 402465Notes

Reaction equation

HRID 402465 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:14][C:15]=2[C:17]([F:20])([F:19])[F:18])[N:10]([CH3:28])[N:9]=1.C1COCC1.O[Li].O.Cl>CCO.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:14][C:15]=2[C:17]([F:20])([F:19])[F:18])[N:10]([CH3:28])[N:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67209388HCID 67209388, compound

Product 1

HCID 67209398HCID 67209398, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(3-(2-fluorophenyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-yloxy)acetate (180 mg, 0.45 mmol) in a mixture of EtOH, THF and water (2 ml/1 ml/0.5 ml) was added LiOH.H2O (76.1 mg, 1.81 mmol). The reaction mixture was stirred for 1 h at rt. Aqueous HCl was then added to adjust the reaction mixture to pH ˜2. The resulting precipitate was filtered off and washed twice with pentane (2×10 mL). The obtained solid was dried under vacuum to furnish 130 mg (78%) of the title compound. [1H-NMR (CDCl3, 300 MHz) δ 7.58-6.95 (m, 5H), 5.25 (s, 2H), 4.15 (s, 3H); LCMS RtA=1.681 min; [M+H]+=370.1]

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed twice with pentane (2×10 mL)
  3. customThe obtained solid was dried under vacuum

Sources & evidence

ORD record
ord-e5c9760dde614bfbbff70dd20f2e5ad1
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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