Lithium Hydroxide → HCID 10274363, compound

HRID 2214950Notes

Reaction equation

HRID 2214950 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-α]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-α]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-09d42f2b6f3d4745b8af3eb22d9025f3
Source dataset
uspto-grants-2006_09
Patent number
US07109209B2

Reaction notes

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