1-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one → HCID 178467139, compound

HRID 526177Notes

Reaction equation

HRID 526177 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].Cl.Cl.[CH3:18][N:19]([CH3:29])[CH2:20][CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([NH2:28])[CH2:24][CH2:23]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:28][C@H:25]1[CH2:26][CH2:27][C@H:22]([CH2:21][CH2:20][N:19]([CH3:18])[CH3:29])[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-oneHCID 178483490HCID 178483490, compound

Product 1

HCID 178467139HCID 178467139, compoundYield 37.3%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (250 mg, 1.0 mmol) was reacted with trans-4-[2-(dimethylamino)ethyl]cyclohexanamine dihydrochloride (300 mg, 1.2 mmol) to afford the desired product (140 mg, 36%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 10.88 (br s, 1H), 8.93 (s, 1H), 8.07 (d, J=8.7 Hz, 1H), 7.52 (d, J=8.8 Hz, 1H), 5.04-4.96 (m, 1H), 2.67 (s, 3H), 2.36-2.22 (m, 4H), 2.24 (s, 6H), 1.93-1.83 (dd, J=13.9, 3.5 Hz, 2H), 1.49-1.31 (m, 5H), 1.27-1.15 (m, 2H); ESI MS m/z 375 [M+H]+

Sources & evidence

ORD record
ord-f3008e5e12ec4c46a9ec8a7e86de9928
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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