Pyridine → HCID 66625224, compound

HRID 2167271Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:6][C@@H:5]1[CH3:22])(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl.C(Cl)(Cl)Cl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([O:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:19][CH:20]=2)[CH2:6][C@@H:5]1[CH3:22])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

[Step 3] (2S,4R)-1-acetyl-4-(4-aminophenoxy)-2-methyl-1,2,3,4-tetrahydroquinoline was dissolved in 2 mL of dichloromethane, and 28.4 μL of pyridine and 19.1 μL of methanesulfonyl chloride were added to the solution at 0° C. The mixture was stirred for 2 hours at 0° C. After completion of the reaction, the reaction mixture was diluted with chloroform, and then was washed with 1 N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and saturated brine. Subsequently, the resultant was dehydrated over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (hexane:acetone=2:1), and then was recrystallized from chloroform-hexane. Thus, 28.2 mg (32.0%, cis-form only) of the title compound was obtained as a pale peach-colored amorphous compound.

Workup

customAfter completion of the reaction
washwas washed with 1 N hydrochloric acid
concentrationwas concentrated under reduced pressure
customThe resulting residue was purified
customwas recrystallized from chloroform-hexane

Sources & evidence

ORD record: ord-43d6a83f8f184f7d84c1ac34a536bd88
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045423B2

Reaction notes

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