1-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one → HCID 178467148, compound

HRID 526175Notes

Reaction equation

HRID 526175 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]([CH3:27])[C@H:20]1[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]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:26][C@H:23]1[CH2:24][CH2:25][C@H:20]([N:19]([CH3:27])[CH3:18])[CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-oneHCID 178484109HCID 178484109, compound

Product 1

HCID 178467148HCID 178467148, compoundYield 45%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (250 mg, 1.0 mmol) was reacted with trans-N1,N1-dimethylcyclohexane-1,4-diamine dihydrochloride (336 mg, 1.6 mmol) to afford the desired product (156 mg, 38%) as a light brown solid: 1H NMR (500 MHz, CDCl3) δ 10.88 (br s, 1H), 8.94 (s, 1H), 8.08 (d, J=8.7 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 5.07-4.92 (m, 1H), 2.67 (s, 3H), 2.34 (s, 6H), 2.39-2.32 (m, 2H), 2.31-2.22 (m, 1H), 2.07-1.99 (m, 2H), 1.56-1.35 (m, 4H); ESI MS m/z 347 [M+H]+

Sources & evidence

ORD record
ord-e6698bed60f244e5a57dfebfb55d6ec0
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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