HCID 15519648, compound → HCID 70157490, compound

HRID 2227485Notes

Reaction equation

COCCOC[O:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([NH:18][CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:17])=[CH:10][CH:9]=1.[ClH:26].CO>>[ClH:26].[OH:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([NH:18][CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[O:17])=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 15519648HCID 15519648, compound

HCID 21893726Hydrochloride methanol

Product 1

HCID 70157490HCID 70157490, compound

Procedure

4.06 g of (E)-3-[4-[(2-methoxyethoxy)methoxy]phenyl]-N-(3-pyridylmethyl)-2-propenoic acid amide was dissolved in 100 ml of 25% HCl/methanol and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure to give (E)-3-(4-hydroxyphenyl)-N-(3-pyridylmethyl)-2-propenoic acid amide hydrochloride as a colorless solid, which was then dissolved in 40 ml dimethylformamide and stirred with 10.2 g of potassium carbonate and 2.5 ml of ethyl bromoacetate at room temperature for 2 hours. After addition of ethyl acetate, the reaction mixture was filtered to remove insoluble products. The resulting filtrate was washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a residue, which was then purified via column chromatography on silica gel (chloroform:methanol=50:1), followed by recrystallization, to provide the compound of interest (2.31 g, 58%).

Workup

customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-f58306e0aaa34c1ea79615d4db787075
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06413995B1

Reaction notes

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