Cyclopropanecarbonyl chloride → N-(2,4-dimethoxybenzyl)-N-(4-iodo-5-methylpyridin-2-yl)cyclopropanecarboxamide

HRID 537028Notes

Reaction equation

CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:13]=1[CH2:14][NH:15][C:16]1[CH:21]=[C:20]([I:22])[C:19]([CH3:23])=[CH:18][N:17]=1.[CH:30]1([C:33](Cl)=[O:34])[CH2:32][CH2:31]1>C(Cl)Cl.[Cl-].[NH4+]>[CH3:10][O:11][C:12]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:13]=1[CH2:14][N:15]([C:16]1[CH:21]=[C:20]([I:22])[C:19]([CH3:23])=[CH:18][N:17]=1)[C:33]([CH:30]1[CH2:32][CH2:31]1)=[O:34]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of DIEA (1.8 mL, 10.4 mmol) in DCM (50 mL) at 0° C. was added N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (2.0 g, 5.2 mmol) and cyclopropanecarbonyl chloride (0.66 mL, 7.3 mmol). The reaction mixture was allowed to stir at 0° C. for 2 h and then diluted with DCM and aqueous ammonium chloride. The aqueous solution was removed and the organic solution was dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give N-(2,4-dimethoxybenzyl)-N-(4-iodo-5-methylpyridin-2-yl)cyclopropanecarboxamide (1.8 g, 78%).

Workup

customThe aqueous solution was removed
dry with materialthe organic solution was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-3703956eaa7042f48b09621e6ad97266
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859768B2

Reaction notes

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