1-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one → HCID 178467145, compound

HRID 526076Notes

Reaction equation

HRID 526076 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].C(O)(=O)C.C(O)(=O)C.[CH3:24][N:25]([CH2:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30][CH2:29]1)[CH3:26]>>[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:34][C@H:31]1[CH2:32][CH2:33][C@H:28]([CH2:27][N:25]([CH3:26])[CH3:24])[CH2:29][CH2:30]1

Participants

3

Reactant 2

HCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-oneHCID 178476567HCID 178476567, compound

Product 1

HCID 178467145HCID 178467145, compoundYield 63%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (360 mg, 1.5 mmol) was reacted with trans-4-[(dimethylamino)methyl]cyclohexanamine diacetic acid salt (500 mg, 1.8 mmol) to afford the desired product (340 mg, 63%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 10.89 (s, 1H), 8.93 (s, 1H), 8.07 (d, J=8.6 Hz, 1H), 7.51 (d, J=8.6 Hz, 1H), 5.16-4.96 (m, 1H), 2.67 (s, 3H), 2.34-2.24 (m, 2H), 2.22 (s, 6H), 2.14 (d, J=7.1 Hz, 2H), 1.98-1.89 (m, 2H), 1.56-1.47 (m, 1H), 1.41-1.32 (m, 2H), 1.28-1.10 (m, 2H); ESI MS m/z 361 [M+H]+; HPLC 98.8% (AUC), tR=8.42 min.

Sources & evidence

ORD record
ord-b0c3538e53c14b4387731040e5f28328
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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