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

HRID 1630413Notes

Reaction equation

HRID 1630413 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:17])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:18][CH:19]1[CH2:24][C:23](=O)[CH2:22][C:21](=[O:26])[CH2:20]1.[NH2:27][C:28]1[NH:32][N:31]=[CH:30][CH:29]=1.C1C([NH:36]C(C)=O)C1>>[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:22]4[C:21](=[O:26])[CH2:20][CH:19]([CH3:18])[CH2:24][C:23]=4[NH:27][C:28]4[NH:32][N:31]=[CH:30][C:29]3=4)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:11]1[CH:14]([CH2:15][C:16]([NH2:36])=[O:17])[CH2:10]1

Participants

4

Reactant 3

HCID 4580955-Methylcyclohexane-1,3-dioneHCID 86676729(E)-3-[5-(3-Fluorophenyl)pyridin-2-yl]propenalHCID 1317317095-amino-1H-pyrazole 3-cyclopropyl methylcarboxamide

Product 1

HCID 1371957984-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-7-methyl-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 200 mg of (E)-3-[5-(3-fluorophenyl)pyridin-2-yl]propenal, 111 mg of 5-methylcyclohexane-1,3-dione and 159 mg of 5-amino-1H-pyrazole-3-cyclopropyl methylcarboxamide.

Sources & evidence

ORD record
ord-218487c6972d4bf388d6e66f72ac38dc
Source dataset
uspto-grants-2014_07
Patent number
US08791133B2

Reaction notes

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