Hydrochloric Acid → 2-[1-[4-(2-naphthamido)benzyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]acetic acid

HRID 589412Notes

Reaction equation

HRID 589412 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:34]=[CH:33][C:17]([CH2:18][N:19]2[C:23]3=[N:24][CH:25]=[CH:26][CH:27]=[C:22]3[C:21]([CH2:28][C:29]([O:31]C)=[O:30])=[N:20]2)=[CH:16][CH:15]=1)=[O:12].O.[OH-].[Li+].Cl>O1CCCC1.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][N:19]2[C:23]3=[N:24][CH:25]=[CH:26][CH:27]=[C:22]3[C:21]([CH2:28][C:29]([OH:31])=[O:30])=[N:20]2)=[CH:33][CH:34]=1)=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 90449071methyl 2-[1-[4-(2-naphthamido)benzyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate

Product 1

HCID 715720462-[1-[4-(2-naphthamido)benzyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]acetic acidYield 49.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 2-[1-[4-(2-naphthamido)benzyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate (60 mg, 0.13 mmol) and lithium hydroxide monohydrate (10 mg, 0.24 mmol) were added into a mixed solution of tetrahydrofuran (5 mL) and water (20 mL), and reacted at room temperature for 2 hours. Tetrahydrofuran was rotate evaporated. The pH was adjusted to 3 with 1 mol/L hydrochloric acid. It was extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The organic phase was rotate evaporated to dryness to obtain a light brown solid 28 mg, at a yield of 49.3%.

Workup

  1. customreacted at room temperature for 2 hours
  2. extractionIt was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe organic phase was rotate evaporated to dryness

Sources & evidence

ORD record
ord-c03b435a702c4f96a47b962d42bd4c99
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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