2-Methoxyethylamine → HCID 58901929, compound

HRID 2233345Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]2[C:16](Cl)=[N:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O:27][CH2:28][CH2:29][NH2:30]>CS(C)=O.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]2[C:16]([NH:30][CH2:29][CH2:28][O:27][CH3:26])=[N:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

-(2-(Benzyloxy)pyridin-4-yl)-N-(2-methoxyethyl)-6-(trifluoromethyl)-pyridin-2-amine. To a 2.5-mL microwave vial was added 3-(2-(benzyloxy)-pyridin-4-yl)-2-chloro-6-(trifluoromethyl)pyridine (0.50 g, 1.37 mmol) and 2-methoxyethylamine (0.59 g, 6.58 mmol, Fluka) in 2 mL of DMSO. The vial was sealed and left to stir at 40° C. for 3 d and then heated at 120° C. for 5 h. The reaction mixture was allowed to cool to room temperature and was diluted with EtOAc (20 mL). The organic layer was washed with saturated NaCl (2×30 mL), dried over Na2SO4, filtered, and concentrated to afford a yellow oil. The crude material was purified by normal phase column chromatography (gradient: 5%-20% EtOAc/Hexanes) to give 3-(2-(benzyloxy)pyridin-4-yl)-N-(2-methoxyethyl)-6-(trifluoromethyl)pyridin-2-amine as a clear oil [MS (ESI, pos. ion) m/z: 404 (M+1)].

Workup

customThe vial was sealed
waitleft
temperatureheated at 120° C. for 5 h
temperatureto cool to room temperature
washThe organic layer was washed with saturated NaCl (2×30 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto afford a yellow oil
customThe crude material was purified by normal phase column chromatography (gradient: 5%-20% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-b1cae573e5b748c2b19c1bd30cffe6f6
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709501B2

Reaction notes

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