Lithium Hydroxide → HCID 131735344, compound

HRID 628270Notes

Reaction equation

HRID 628270 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]4[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=4)[C:19]([O:21]C)=[O:20])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[Li+].[OH-].O[Li].O>O1CCOCC1.O.CO>[NH4+:3].[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]4[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=4)[C:19]([O-:21])=[O:20])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 118159879HCID 118159879, compound

Product 1

HCID 131735344HCID 131735344, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 3-[(1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-6-yl)methyl]benzoate (0.090 g, 0.27 mmol, prepared as in Example 26, Step 1) in 1,4-dioxane (2 mL), H2O (1 mL) and MeOH (1 mL) was added LiOH, monohydrate (0.056 g, 1.3 mmol) and the reaction was stirred overnight. Further LiOH—H2O (0.050 g, 1.1 mmol) was added and the reaction was continued for 8 hours. The reaction mixture was diluted with additional water, filtered and purified via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (74 mg, 86%).

Workup

  1. waitthe reaction was continued for 8 hours
  2. filtrationfiltered
  3. custompurified via preparative HPLC-MS (Waters XBridge C18
  4. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (74 mg, 86%)

Sources & evidence

ORD record
ord-0c40608a9293431e9d166c798b617cd7
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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