Dimedone → 4-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-7,7-dimethyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline 3-cyclopropylmethylcarboxamide

HRID 1630410Notes

Reaction equation

HRID 1630410 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[CH:16]=O)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:18][C:19]1[NH:23][N:22]=[CH:21][CH:20]=1.[CH2:24]1[CH:26]([CH2:27][C:28]([NH2:30])=[O:29])[CH2:25]1.[CH3:31][C:32]1([CH3:40])[CH2:39][C:37](=O)[CH2:36][C:34](=[O:35])[CH2:33]1>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[CH:16]3[C:36]4[C:34](=[O:35])[CH2:33][C:32]([CH3:40])([CH3:31])[CH2:39][C:37]=4[NH:18][C:19]4[NH:23][N:22]=[CH:21][C:20]3=4)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:25]1[CH:26]([CH2:27][C:28]([NH2:30])=[O:29])[CH2:24]1

Participants

5

Reactant 3

HCID 31358DimedoneHCID 86676729(E)-3-[5-(3-Fluorophenyl)pyridin-2-yl]propenalHCID 1317317005-Amino-1H-pyrazole 3-cyclopropylmethylcarboxamide

Product 1

HCID 1371957924-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-7,7-dimethyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline 3-cyclopropylmethylcarboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to general procedure A, a mixture of 50 mg of (E)-3-[5-(3-fluorophenyl)pyridin-2-yl]propenal, 40 mg of 5-amino-1H-pyrazole-3-cyclopropylmethylcarboxamide, 31 mg of dimedone and 5 ml of ethanol is boiled under reflux for 2 hours. After cooling, the mixture is concentrated and purified by column chromatography (silica gel, methanol:DCM=5:95).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. custompurified by column chromatography (silica gel, methanol:DCM=5:95)

Sources & evidence

ORD record
ord-0c7f95533d2a4440bdf1247e41b6a23c
Source dataset
uspto-grants-2014_07
Patent number
US08791133B2

Reaction notes

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