4-(2-Dimethylaminoethyl)aniline → 1-(6-Chloro-4-{4-[2-(dimethylamino)ethyl]phenylamino}-1,5-naphthyridin-3-yl)ethanone

HRID 2178911Notes

Reaction equation

HRID 2178911 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14].[CH3:16][N:17]([CH3:27])[CH2:18][CH2:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>>[Cl:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13](=[O:15])[CH3:14])=[C:2]2[NH:24][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][N:17]([CH3:16])[CH3:27])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 149398614-(2-Dimethylaminoethyl)anilineHCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one

Product 1

HCID 1177738421-(6-Chloro-4-{4-[2-(dimethylamino)ethyl]phenylamino}-1,5-naphthyridin-3-yl)ethanoneYield 60.6%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (150 mg, 0.64 mmol) was reacted with 4-[2-(dimethylamino)ethyl)aniline (110 mg, 0.64 mmol) to afford the desired product (143 mg, 60%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 10.86 (br s, 1H), 8.99 (s, 1H), 8.14 (d, J=8.8 Hz, 1H), 7.50 (d, J=8.8 Hz, 1H), 7.22-7.15 (m, 2H), 7.11-7.04 (m, 2H), 2.87 (t, J=8.1 Hz, 2H), 2.70-2.60 (m, 2H), 2.55 (s, 3H), 2.39 (s, 6H); ESI MS m/z 369 [M+H]+

Sources & evidence

ORD record
ord-83c0c939b34049baba105aacd26fd84e
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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