6-Hydroxyquinoline → 2-(6-quinolinyloxy)-N-(1-methoxy-4-methylpent-2-yn-4-yl) 3-methoxypropionamide

HRID 1244817Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.Br[CH:13]([CH2:25][O:26][CH3:27])[C:14]([NH:16][C:17]([CH3:24])([CH3:23])[C:18]#[C:19][CH2:20][O:21][CH3:22])=[O:15]>>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][CH:13]([CH2:25][O:26][CH3:27])[C:14]([NH:16][C:17]([CH3:24])([CH3:23])[C:18]#[C:19][CH2:20][O:21][CH3:22])=[O:15])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 113746-Hydroxyquinoline

HCID 21078403HCID 21078403, compound

Product 1

HCID 692550632-(6-quinolinyloxy)-N-(1-methoxy-4-methylpent-2-yn-4-yl) 3-methoxypropionamide

Procedure

In a similar procedure to Example 6 Stage 2, 6-hydroxyquinoline was reacted with 2-bromo-N-(1-methoxy-4-methylpent-2-yn-4-yl) 3-methoxypropionamide to give 2-(6-quinolinyloxy)-N-(1-methoxy-4-methylpent-2-yn-4-yl) 3-methoxypropionamide as a colourless oil. 1H NMR (CDCl3) δ: 1.60(3H, s); 1.62(3H, s); 3.34(3H, s); 3.44(3H, s); 3.90–3.94(2H, m); 4.06(2H, s); 4.76–4.80(1H, m); 6.60(1H, s); 7.14–7.16(1H, m); 7.36–7.40(1H, m); 7.46–7.50(1H, m); 8.04–8.08(2H, d); 8.82–8.84(1H, m).

Sources & evidence

ORD record: ord-0707f4a00a6e42288320eb46fc41c90b
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122672B2

Reaction notes

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