1-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one → HCID 178467151, compound

HRID 526185Notes

Reaction equation

HRID 526185 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].[NH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]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:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-oneHCID 178511715HCID 178511715, compound

Product 1

HCID 178467151HCID 178467151, compoundYield 78.2%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (480 mg, 2.0 mmol) was reacted with trans-4-aminocyclohexanol (287 mg, 2.5 mmol) to afford the desired product (500 mg, 78%) as an orange-red solid: 1H NMR (500 MHz, CDCl3) δ 10.90 (s, 1H), 8.95 (s, 1H), 8.09 (d, J=8.7 Hz, 1H), 7.53 (d, J=8.7 Hz, 1H), 5.10 (tdt, J=11.2, 8.0, 3.9 Hz, 1H), 3.76 (tt, J=10.0, 4.3 Hz, 1H), 2.68 (s, 3H), 2.33-2.24 (m, 2H), 2.13-2.04 (m, 2H), 1.63-1.41 (m, 8H); ESI MS m/z 320 [M+H]+

Sources & evidence

ORD record
ord-7b5eaa25417248d9afc2cf0e105785b2
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

Loading…