Hydrochloric Acid → HCID 136376519, compound

HRID 402473Notes

Reaction equation

HRID 402473 reaction equation
[OH-:1].[Na+].Cl[C:4]1[N:9]=[C:8]2[N:10]([CH3:19])[N:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]2=[CH:6][CH:5]=1.Cl>CS(C)=O>[CH3:19][N:10]1[C:8]2[NH:9][C:4](=[O:1])[CH:5]=[CH:6][C:7]=2[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86672048HCID 86672048, compound

Product 1

HCID 136376519HCID 136376519, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of aqueous NaOH (0.64 g, 16.00 mmol in 2.0 mL H2O) and 6-chloro-1-methyl-3-phenyl-1H-pyrazolo[3,4-b]pyridine (0.39 g, 1.6 mmol) in DMSO (2.0 mL) was heated at 100° C. for 10 h. The reaction mixture was cooled to rt and neutralized with diluted HCl. A white solid was obtained. The solid was collected by filtration, washed with diethyl ether and dried under vacuum to yield the title compound as white solid (0.345 g, 96%). [1H-NMR (DMSO-d6, 300 MHz) δ 8.27 (d, 1H), 7.92 (m, 2H), 7.55-7.35 (m, 3H), 6.46 (d, 1H), 3.9 (s, 3H); HPLC RtA=6.802 min (99.7%); LCMS RtA=0.360 min; [M+H]+=226.0]

Workup

  1. customA white solid was obtained
  2. filtrationThe solid was collected by filtration
  3. washwashed with diethyl ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-493ddb76784d43538f5b6c162791c348
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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