Hydrogen chloride-ethyl acetate → 1-methyl-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridine

HRID 1399883Notes

Reaction equation

HRID 1399883 reaction equation
[CH3:1][N:2]1[C:6]2[CH2:7][N:8](C(OC(C)(C)C)=O)[CH2:9][CH2:10][C:5]=2[CH:4]=[N:3]1.Cl.CC(=O)OCC>CC(=O)OCC>[CH3:1][N:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 71711049tert-Butyl 1-methyl-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate

Product 1

HCID 707011991-methyl-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridineYield 28%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred mixture of tert-butyl 1-methyl-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate (744 mg, 3.14 mmol) in EA (2 mL) was added HCl/EA (3N, 4 mL). The mixture was stirred at 25° C. for 16 hours. The reaction mixture was then concentrated and the residue purified by Prep-HPLC and SFC to afford the target compound as colorless oil which was used without further purification in the next step. (120 mg; yield 28%). LCMS (m/z): 138.10 (M+1).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue purified by Prep-HPLC and SFC

Sources & evidence

ORD record
ord-9a6aee190ec149b9a2dc1c833f447805
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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