Diisopropylethylamine → N-(2-(tert-butylamino)pyridin-3-yl)-2,3-difluorobenzamide

HRID 253967

Reaction equation

[C:1]([NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[F:22][C:23]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C(Cl)Cl>[C:1]([NH:5][C:6]1[C:11]([NH:12][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:23]=2[F:22])=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N2-tert-butylpyridine-2,3-diamine in dry DCM (150 mL) was added DIEA (17 mL, 95.5 mmol). The solution was cooled to 0° C. and carefully added 2,3-difluorobenzoyl chloride (8.35 g, 47.30 mmol). The reaction was allowed to warm up to RT and stirred for 1 hr. The mixture was then washed with water, saturated NaHCO3, and dried over MgSO4. Removal of the solvent by evaporation, the residue was purified by silica gel chromatography (5%-60% EtOAc/hexane) to yield N-(2-(tert-butylamino)pyridin-3-yl)-2,3-difluorobenzamide (4.0 g, 13.10 mmol); LC-MS m/e=306.1 (M+H).

Workup

temperatureto warm up to RT
washThe mixture was then washed with water, saturated NaHCO3
dry with materialdried over MgSO4
customRemoval of the solvent
customby evaporation
customthe residue was purified by silica gel chromatography (5%-60% EtOAc/hexane)

Sources & evidence

ORD record: ord-ef7d54834db9401fa8d9e04131ed7fd6
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872031B2

Linked notes

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