1-(4-Methoxyphenyl)-2,2-dimethylcyclopropanecarbonyl chloride → 1-(4-methoxyphenyl)-2,2-dimethyl-N-(6-(4-(N-methylsulfamoyl)-phenyl)pyridin-2-yl)cyclo-propanecarboxamide

HRID 2420921Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:14](Cl)=[O:15])[CH2:11][C:10]2([CH3:13])[CH3:12])=[CH:5][CH:4]=1.Cl.[NH2:18][C:19]1[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([NH:34][CH3:35])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:14]([NH:18][C:19]3[CH:20]=[CH:21][CH:22]=[C:23]([C:25]4[CH:26]=[CH:27][C:28]([S:31](=[O:33])(=[O:32])[NH:34][CH3:35])=[CH:29][CH:30]=4)[N:24]=3)=[O:15])[CH2:11][C:10]2([CH3:13])[CH3:12])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-(4-Methoxyphenyl)-2,2-dimethylcyclopropanecarbonyl chloride (0.20 mmol) was added to a solution of 4-(6-aminopyridin-2-yl)-N-methylbenzenesulfonamide HCl salt (60 mg, 0.20 mmol) in pyridine (1 mL) at room temperature. The reaction was stirred at 60° C. overnight and then was concentrated, dissolved in DMSO and purified by LC-MS to yield 1-(4-methoxyphenyl) -2,2-dimethyl-N-(6-(4-(N-methylsulfamoyl)-phenyl)pyridin-2-yl)cyclo-propanecarboxamide. ESI-MS m/z calc. 465.2, found 466.5 (M+1)+. Retention time 1.98 minutes.

Workup

concentrationwas concentrated
dissolutiondissolved in DMSO
custompurified by LC-MS

Sources & evidence

ORD record: ord-83fe88a720504cdb80d4f72f6f793d6e
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956052B2

Reaction notes

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