N2-(2-(dimethylamino)ethyl)pyridine-2,5-diamine → 1-(6-Chloro-4-{6-[2-(dimethylamino) ethylamino]pyridin-3-ylamino}-1,5-naphthyridin-3-yl)ethanone

HRID 2178918Notes

Reaction equation

HRID 2178918 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]([CH3:28])[CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][N:22]=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:27][C:24]1[CH:23]=[N:22][C:21]([NH:20][CH2:19][CH2:18][N:17]([CH3:28])[CH3:16])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 16772731N2-(2-(dimethylamino)ethyl)pyridine-2,5-diamineHCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one

Product 1

HCID 1177730661-(6-Chloro-4-{6-[2-(dimethylamino) ethylamino]pyridin-3-ylamino}-1,5-naphthyridin-3-yl)ethanoneYield 45.5%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (300 mg, 1.2 mmol) was reacted with N2-[2-(dimethylamino)ethyl]pyridine-2,5-diamine (320 mg, 1.5 mmol) to afford the desired product (210 mg, 37%) as an orange solid: 1H NMR (500 MHz, CDCl3) δ 11.41 (br s, 1H), 9.02 (s, 1H), 8.13-8.07 (m, 1H), 7.95 (d, J=2.5 Hz, 1H), 7.47 (dd, J=8.7, 1.1 Hz, 1H), 7.29-7.23 (m, 1H), 6.44 (d, J=8.8 Hz, 1H), 5.12 (t, J=5.1 Hz, 1H), 3.41 (q, J=5.7 Hz, 2H), 2.69 (s, 3H), 2.60 (t, J=6.0 Hz, 2H), 2.30 (s, 6H); ESI MS m/z 385 [M+H].+

Sources & evidence

ORD record
ord-6609e1053aea4ae582bd4696f6b831f2
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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