7-Isoquinolinol → 2-(7-isoquinolinyloxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide

HRID 2222294Notes

Reaction equation

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

Participants

Reactant 2

HCID 4597677-Isoquinolinol

HCID 210784052-bromo-3-methoxy-N-(4-methylpent-2-yn-4-yl)propionamide

Product 1

HCID 219231152-(7-isoquinolinyloxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide

Procedure

In a similar procedure to Example 6, 7-hydroxyisoquinoline (commercially available) and 2-bromo-N-(4-methylpent-2-yn-4-yl) 3-methoxypropionamide were reacted to give 2-(7-isoquinolinyloxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide (Compound No. 2 of Table 49) as a colourless solid, m.p. 155-156° C.

Sources & evidence

ORD record: ord-7896302eb0be4b07858a8d15dc6daf74
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371764B2

Reaction notes

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