Dimethylformamide → 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide

HRID 2080276Notes

Reaction equation

Cl[C:2]1[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:5].[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[CH2:23][CH2:24][NH2:25].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[Cl:18][C:16]1[CH:15]=[CH:14][C:3]([C:4]([NH:6][CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:5])=[C:2]([NH:25][CH2:24][CH2:23][C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([F:19])[CH:21]=2)[N:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,6-dichloro-N-(pyridin-3-ylmethyl)nicotinamide (20.4 g, 72.3 mmol), 3-fluorophenethyl amine (11.1 g, 79.5 mmol), K2CO3 (20 g 145 mmol) and DMF (200 mL) was stirred at 100° C. for 10 hours. The mixture was diluted with ethyl acetate (2×300 mL) and washed with saturated ammonium chloride, sodium bicarbonate and brine. The organic layers were combined, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography to give 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (12.6 g, 46%). LRMS (M+H+) m/z 385.1.

Workup

washwashed with saturated ammonium chloride, sodium bicarbonate and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-60903f7240f44134907988e09c2c190b
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932270B2

Reaction notes

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