Lithium Hydroxide → HCID 10274363, compound

HRID 1797072Notes

Reaction equation

HRID 1797072 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)=[N:15][N:16]4[C:21]([CH3:22])=[C:20]([C:23]([O:25]CC)=[O:24])[CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>O1CCOCC1>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)=[N:15][N:16]4[C:21]([CH3:22])=[C:20]([C:23]([OH:25])=[O:24])[CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10298190HCID 10298190, compound

Product 1

HCID 10274363HCID 10274363, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-7-methylpyrazolo[1,5-a]pyridine-6-carboxylate (40 mg, 0.087 mmol) in dioxane (600 μL) was added lithium hydroxide (300 μL, 1M aqueous, 0.30 mmol). The reaction mixture was stirred at room temperature 16 hours. The reaction mixture was concentrated in vacuo to remove dioxane, then diluted with water. The aqueous mixture was acidified with 1 N aqueous hydrochloric acid. Upon standing for 72 hours, a solid precipitate had formed which was collected by filtration to provide 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-7-methylpyrazolo[1,5-a]pyridine-6-carboxylic acid (31 mg, 82%). Rf 0.10 (19:1 dichloromethane:methanol); MS m/z 432 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove dioxane
  3. additiondiluted with water
  4. waitUpon standing for 72 hours
  5. customa solid precipitate had formed which
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-ff1421c999154081977b429fd5983979
Source dataset
uspto-grants-2006_04
Patent number
US07034030B2

Reaction notes

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