Sulfuric Acid → HCID 178433995, compound

HRID 1062577Notes

Reaction equation

HRID 1062577 reaction equation
[OH:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]2=[CH:4][C:3]=1[C:13]#[N:14].[OH:15]S(O)(=O)=O>>[OH:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]2=[CH:4][C:3]=1[C:13]([NH2:14])=[O:15]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 178433994HCID 178433994, compound

Product 1

HCID 178433995HCID 178433995, compound

Conditions

Temperature
40 °C

Procedure

6-Hydroxy-1,3-dimethylpyrazolo[5,4-b]pyridine-5-carbonitrile (0.91 g) was dissolved in concentrated H2SO4 (3 mL) and stirred at 40° C. for 24 hours. The solution was poured into ice water and the precipitate was filtered, washed with water, and dried under high vacuum to give 6-hydroxy-1,3-dimethylpyrazolo[5,4-b]pyridine-5-carboxamide as a white solid. A portion of this material (0.12 g) was dissolved in DMF (2 mL) and treated with 1-(2-chloroethyl)pyrrolidine hydrochloride (0.12 g) and potassium carbonate (0.30 g). The reaction mixture was stirred at 60° C. for 18 h, poured into water, and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution and brine, dried over Na2SO4 and concentrated under reduced pressure to give 1,3-dimethyl-6-[2-(pyrrolidin-1-yl)-ethoxy]-1H-pyrazolo[3,4-b]pyridine-5-carboxamide. A portion of this material (0.06 g) was dissolved in toluene and treated with 3-isopropoxyphenyl isocyanate (0.1 g). The mixture was heated at reflux for 23 hours, and then cooled to room temperature. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (methanol/ethyl acetate). A portion of this material was dissolved in tetrahydrofuran and treated with 4M HCl/dioxane. The solid material obtained was recrystallized from acetonitrile to give 1-{1,3-dimethyl-6-[2-(pyrrolidin-1-yl)ethoxy]-1H-pyrazolo[3,4-b]pyridine-5-carbonyl}-3-(3-isopropoxyphenyl)urea hydrochloride (1), as a white solid.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-f7ec81e4d79d4ef18bdfed07e3dcded9
Source dataset
uspto-grants-2005_11
Patent number
US06962926B2

Reaction notes

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