Triethylamine → HCID 69145639, compound

HRID 2218247Notes

Reaction equation

[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH:7]=[C:6]([C:26]2[CH:31]=[CH:30][C:29](Cl)=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=2)[C:3]=1[C:4]#[N:5].[CH2:36]([N:38](CC)[CH2:39]C)C.Cl.CNC>CN(C=O)C>[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH:7]=[C:6]([C:26]2[CH:31]=[CH:30][C:29]([N:38]([CH3:39])[CH3:36])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=2)[C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 2-amino-4-(4-chloro-3-nitrophenyl)-6-{2-[(4-methoxybenzyl)oxy]phenyl}-nicotinonitrile (0.850 g, 1.746 mmol) in DMF (5 mL) including triethylamine (1.2 mL) was added dimethylamine hydrochloride (0.996 g, 12.220 mmol), and the mixture was stirred at 70° C. for 3 hrs. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was suspended in ethanol. The resulting solid was collected by filtration, washed with ethanol, and dried under reduced pressure to give 2-amino-4-[4-(dimethylamino)-3-nitrophenyl]-6-{2-[(4-methoxybenzyl)-oxy]phenyl}nicotinonitrile as an orange oil (0.820 g, yield 95%).

Workup

customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate
washThe organic phase was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
filtrationThe resulting solid was collected by filtration
washwashed with ethanol
customdried under reduced pressure

Sources & evidence

ORD record: ord-ab5d990f32f048f5983b3ead8b65a9ff
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410986B2

Reaction notes

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