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

HRID 1630412Notes

Reaction equation

HRID 1630412 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.[CH:18]([CH:21]1[CH2:26][C:25](=O)[CH2:24][C:23](=[O:28])[CH2:22]1)([CH3:20])[CH3:19].[NH2:29][C:30]1[NH:34][N:33]=[CH:32][CH:31]=1.[CH2:35]1[CH:37]([CH2:38][C:39]([NH2:41])=[O:40])[CH2:36]1>>[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:24]4[C:23](=[O:28])[CH2:22][CH:21]([CH:18]([CH3:19])[CH3:20])[CH2:26][C:25]=4[NH:29][C:30]4[NH:34][N:33]=[CH:32][C:31]3=4)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:36]1[CH:37]([CH2:38][C:39]([NH2:41])=[O:40])[CH2:35]1

Participants

4

Reactant 3

HCID 5661065-(Isopropyl)cyclohexane-1,3-dioneHCID 86676729(E)-3-[5-(3-Fluorophenyl)pyridin-2-yl]propenalHCID 1317317005-Amino-1H-pyrazole 3-cyclopropylmethylcarboxamide

Product 1

HCID 1371957964-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-7-isopropyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline 3-cyclopropylmethylcarboxamide

Procedure

The title compound is prepared as a mixture of diastereomers according to procedure A from 50 mg of (E)-3-[5-(3-fluorophenyl)pyridin-2-yl]propenal, 34 mg of 5-isopropylcyclohexane-1,3-dione and 40 mg of 5-amino-1H-pyrazole-3-cyclo-propylmethylcarboxamide.

Sources & evidence

ORD record
ord-4f83387cf10c4623ade7e590d58a0440
Source dataset
uspto-grants-2014_07
Patent number
US08791133B2

Reaction notes

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