1-(6-Ethoxy-5-formyl-3-pyridylsulfonyl)-4-ethylpiperazine → 4-{6-ethoxy-5-[3-ethyl-4,5,6,7-tetrahydro-7-oxo-2-(2-pyridylmethyl)-2H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-pyridinylsulfonyl}-1-ethylpiperazine

HRID 1831475Notes

Reaction equation

HRID 1831475 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[CH:21]=O)[CH3:2].[NH2:23][C:24]1[C:25]([C:38]([NH2:40])=[O:39])=[N:26][N:27]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[C:28]=1[CH2:29][CH3:30]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[N:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]2)(=[O:11])=[O:12])=[CH:6][C:5]=1[CH:21]1[NH:23][C:24]2=[C:28]([CH2:29][CH3:30])[N:27]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[N:26]=[C:25]2[C:38](=[O:39])[NH:40]1)[CH3:2]

Participants

4

Reactant 2

HCID 220522361-(6-Ethoxy-5-formyl-3-pyridylsulfonyl)-4-ethylpiperazineHCID 220522374-amino-5-ethyl-1-(2-pyridylmethyl)-1H-pyrazole-3-carboxamide

Product 1

HCID 220522334-{6-ethoxy-5-[3-ethyl-4,5,6,7-tetrahydro-7-oxo-2-(2-pyridylmethyl)-2H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-pyridinylsulfonyl}-1-ethylpiperazineYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(6-ethoxy-5-formyl-3-pyridylsulfonyl)-4-ethylpiperazine(1.1 g, 4.9 mmol, from step (a) above) and 4-amino-5-ethyl-1-(2-pyridylmethyl)-1H-pyrazole-3-carboxamide (1.2 g, 4.9 mmol) in toluene (10 mL) was heated to reflux for 4 hours and the solution was concentrated under vacuum. The resulting product was recrystallised from ethyl acetate to give a pale brown solid (1.4 g, 52%).

Workup

  1. temperatureto reflux for 4 hours
  2. concentrationthe solution was concentrated under vacuum
  3. customThe resulting product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-806039f3b87c4aab968ec134fb833c16
Source dataset
uspto-grants-2006_06
Patent number
US07067660B2

Reaction notes

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