1-Methyl-3-phenyl-1H-pyrazol-5-amine → 4,7-dihydro-1,6-dimethyl-4-(2,5-dimethylphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid ethyl ester, hydrochloride

HRID 1031526Notes

Reaction equation

HRID 1031526 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:3]1.[CH2:14]([O:16][C:17](=[O:31])[C:18](=[CH:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[CH3:30])[C:19]([CH3:21])=O)[CH3:15].[ClH:32].C(OCC)C>C(OCC)C>[ClH:32].[CH2:14]([O:16][C:17]([C:18]1[CH:22]([C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=2[CH3:30])[C:5]2[C:4]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[N:3][N:2]([CH3:1])[C:6]=2[NH:7][C:19]=1[CH3:21])=[O:31])[CH3:15]

Participants

5

Reactant 3

HCID 5177791-Methyl-3-phenyl-1H-pyrazol-5-amineHCID 10953452Ether hydrochlorideHCID 54285001Ethyl-2-(2,5-dimethylbenzyliden)acetoacetate

Product 1

HCID 1372254614,7-dihydro-1,6-dimethyl-4-(2,5-dimethylphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid ethyl ester, hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Starting from 1-methyl-3-phenyl-5-pyrazolamine and ethyl-2-(2,5-dimethylbenzyliden)acetoacetate in equimolar proportions. The crude reaction product is taken up with ethyl ether, washed with 2% H2SO4, water, and then 5% NaHCO3 until neutralization of the mother liquors. After drying over Na2SO4 the hydrochloride of the title compound is obtained by reacting with HCl/ethyl ether. Crystallization from isopropanol/ethyl ether.

Workup

  1. customThe crude reaction product
  2. washwashed with 2% H2SO4, water
  3. dry with materialAfter drying over Na2SO4 the hydrochloride of the title compound
  4. customis obtained
  5. customCrystallization from isopropanol/ethyl ether

Sources & evidence

ORD record
ord-bde35e311a2043e39e8790be6956d6ce
Source dataset
uspto-grants-1990_09
Patent number
US04954508

Reaction notes

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