Lithium Hydroxide → HCID 66732739, compound

HRID 1966849Notes

Reaction equation

HRID 1966849 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[CH2:18][C:17]4([CH2:23][CH2:22][CH:21]([C:24]([O-:26])=[O:25])[CH2:20][CH2:19]4)[O:16][N:15]=3)=[CH:12][N:11]=[C:10]3[N:27]([CH2:30][CH3:31])[N:28]=[CH:29][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.O>[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[CH2:18][C:17]4([CH2:19][CH2:20][CH:21]([C:24]([OH:26])=[O:25])[CH2:22][CH2:23]4)[O:16][N:15]=3)=[CH:12][N:11]=[C:10]3[N:27]([CH2:30][CH3:31])[N:28]=[CH:29][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86647605HCID 86647605, compound

Product 1

HCID 66732739HCID 66732739, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (cis or trans) 3-[4-(cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylate (130 mg, 0.000286 mole) (example 9) was taken in tetrahydrofuran (5 ml). Aqueous lithium hydroxide (48 mg, 0.00147 mole) in 2 ml water was added to it. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The mixture was acidified with 3N hydrochloric acid to about pH of 6. The extraction was done with ethyl acetate. The organic layer was washed with water and brine, dried and concentrated under reduced pressure to get crude product. The title compound was purified by preparative thin layer chromatography.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe extraction
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto get crude product
  7. customThe title compound was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-c948cf79ab654b019f692529556775f1
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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