6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde → 6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

HRID 906327Notes

Reaction equation

HRID 906327 reaction equation
Cl[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[CH:13]=[O:14].[CH:15]1([CH2:20][NH:21][CH2:22][CH3:23])[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH:15]1([CH2:20][N:21]([CH2:22][CH3:23])[C:2]2[N:7]=[C:6]3[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]3=[CH:4][C:3]=2[CH:13]=[O:14])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 162286606-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeHCID 43163716N-(cyclopentylmethyl)-N-ethylamine

Product 1

HCID 574868046-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeYield 178.3%

Conditions

Temperature
100 °C

Procedure

6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (3.90 g, 18.6 mmol) and N-(cyclopentylmethyl)-N-ethylamine (11.70 g, 92.0 mmol) synthesized by the method described in International Patent Publication WO2006/073973 were mixed, and the mixture was stirred at 100° C. for 8 hours in an argon atmosphere. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→5:1) to obtain 6-[(cyclopentylmethyl)(ethyl)amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine 5-carbaldehyde (9.96 g, 99%) as yellow oil.

Workup

  1. additionwere mixed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→5:1)

Sources & evidence

ORD record
ord-4a785709dabb46db9bbc3fcb840138ba
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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