Lithium Hydroxide → HCID 66679413, compound

HRID 902034Notes

Reaction equation

HRID 902034 reaction equation
C[O:2][C:3](=[O:32])[CH:4]=[CH:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:16]3[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=4)=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=34)=[CH:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.C1COCC1.[Li+].[OH-]>O>[NH3:13].[CH3:31][C:27]1[N:26]=[C:25]([C:17]2[C:16]([C:10]3[C:9]4[C:14](=[CH:15][C:6]([CH:5]=[CH:4][C:3]([OH:32])=[O:2])=[CH:7][CH:8]=4)[N:13]=[CH:12][CH:11]=3)=[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][N:19]3[N:18]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66678632HCID 66678632, compound

Product 2

HCID 222AmmoniaHCID 66679413HCID 66679413, compoundYield 182.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-{4-[2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinolin-7-yl}-acrylic methyl ester (0.03 g, 0.07 mmol), THF (1 mL), and H2O (0.5 mL), add LiOH (0.012 g, 0.29 mmol). Stir the reaction mixture at room temperature for 24 hours. Evaporate the solvents in vacuo. Chromatograph the residue on SCX ion-exchange resin (elute with 95% methanol/ethyl acetate, then 100% methanol, then 2M NH3 in methanol) to afford the title compound 26 mg (93%) as a yellowish solid.

Workup

  1. customEvaporate the solvents in vacuo
  2. washChromatograph the residue on SCX ion-exchange resin (elute with 95% methanol/ethyl acetate

Sources & evidence

ORD record
ord-c2995dda8d1f4c4a8f990c0f5ddc496f
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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