diethyl ({[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]amino}methylidene)propanedioate → HCID 178469630, compound

HRID 2070022Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[C:5](=[CH:11][NH:12][C:13]1[N:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:15]=[CH:16][CH:17]=1)[C:6]([O:8]CC)=O)[CH3:2]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[C:6]([OH:8])=[C:17]2[CH:16]=[N:15][N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:13]2=[N:12][CH:11]=1)=[O:27])[CH3:2]

Participants

Conditions

Temperature: 240 °C

Procedure

2-{([2-(4-Methoxybenzyl)-2H-pyrazol-3-ylamino]methylene}malonic acid diethyl ester (7.0 g) was dissolved in diphenyl ether (about 21 mL), the resulting mixture was stirred at 240° C. for 5 hours. The reaction solution was purified by silica-gel column chromatography (dichloromethane/methanol=100/0 to 100/1) to give 4-hydroxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (4.0 g, yield: 65%) as a light-yellow powder.

Workup

customThe reaction solution was purified by silica-gel column chromatography (dichloromethane/methanol=100/0 to 100/1)

Sources & evidence

ORD record: ord-4f96f39d1f45486ea17c57e64ddc9874
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299252B2

Reaction notes

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