HCID 12985697, compound → HCID 12985709, compound

HRID 2119621Notes

Reaction equation

HRID 2119621 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:11]=[N:12][N:13]([CH3:18])[C:14]=2[C:15]([OH:17])=O)[CH:6]=[CH:7][CH:8]=1)[CH3:2].FC1C=C(NC2C=NN(C)C=2C(O)=O)C=CC=1.ClC1C2C(CC)=CC=CC=2N=C2C=NN(C)C=12.ClC1C2C=CC(CC)=CC=2N=C2C=NN(C)C=12>C(O)(=O)C>[CH2:1]([C:3]1[C:4]2[C:15](=[O:17])[C:14]3[N:13]([CH3:18])[N:12]=[CH:11][C:10]=3[NH:9][C:5]=2[CH:6]=[CH:7][CH:8]=1)[CH3:2].[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]2[C:15](=[O:17])[C:14]3[N:13]([CH3:18])[N:12]=[CH:11][C:10]=3[NH:9][C:5]=2[CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 12985697HCID 12985697, compoundHCID 12985708HCID 12985708, compoundHCID 23442411HCID 23442411, compoundHCID 23442415HCID 23442415, compound

Product 2

HCID 9942680HCID 9942680, compoundYield 41%HCID 12985709HCID 12985709, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-[(3-Ethylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid (EXAMPLE 8 and 9, step 1) was treated according to the procedure of step 2 in EXAMPLE 3 instead of 4-[(3-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid. The obtained inseparable mixture of 9-chloro-8-ethyl-1-methyl-1H-pyrazolo[4,3-b]quinoline and 9-chloro-6-ethyl-1-methyl-1H-pyrazolo[4,3-b]quinoline (200 mg, 0.81 mmol) in 50% aqueous acetic acid (8 ml) was refluxed for 8 h. After cooling to room temperature, the mixture was concentrated and chromatographed on a column of silica gel with ethyl acetate/hexane (1:2) to afford 75 mg (41%) of 8-ethyl-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one as a solid and 103 mg (56%) of 6-ethyl-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one as a solid.

Workup

  1. temperaturewas refluxed for 8 h
  2. concentrationthe mixture was concentrated
  3. customchromatographed on a column of silica gel with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-66cf545285df4e63ad10af6c822a30ae
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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