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

HRID 1630419Notes

Reaction equation

HRID 1630419 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[CH:10]=[O:11])=[N:6][CH:7]=1.[CH3:12][C:13]1([CH3:21])[CH2:20][C:18](=O)[CH2:17][C:15](=[O:16])[CH2:14]1.[NH2:22][C:23]1[NH:27][N:26]=[CH:25][CH:24]=1.C1C([NH:31]C(C)=O)C1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[CH:10]2[C:17]3[C:15](=[O:16])[CH2:14][C:13]([CH3:12])([CH3:21])[CH2:20][C:18]=3[NH:22][C:23]3[NH:27][N:26]=[CH:25][C:24]2=3)=[N:6][CH:7]=1.[CH2:5]1[CH:8]([CH2:9][C:10]([NH2:31])=[O:11])[CH2:4]1

Participants

4

Reactant 3

HCID 31358DimedoneHCID 866767303-(5-Bromopyridin-2-yl)prop-2-enalHCID 1317317095-amino-1H-pyrazole 3-cyclopropyl methylcarboxamide

Product 1

HCID 1371958004-[(E)-2-(5-Bromopyridin-2-yl)vinyl]-7,7-dimethyl-5-oxo-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline 3-cyclopropylmethylcarboxamide

Procedure

The title compound is prepared analogously to procedure A from 150 mg of (E)-3-(5-bromopyridin-2-yl)propenal, 100 mg of dimedone and 127 mg of 5-amino-1H-pyrazole-3-cyclopropyl methylcarboxamide.

Sources & evidence

ORD record
ord-61630322f84d4471b97bc6945497a243
Source dataset
uspto-grants-2014_07
Patent number
US08791133B2

Reaction notes

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