Ammonia → 5-Acetyl-2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)benzamide

HRID 1611692Notes

Reaction equation

HRID 1611692 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:13])=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10])(=[O:3])[CH3:2].[OH:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18](OC)=O.[NH3:25]>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:2][CH2:1][CH2:4][CH:5]([O:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:17]3[C:16]=2[N:25]=[C:9]([NH2:11])[CH:8]=[CH:18]3)[CH3:6])=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 88068Methyl 3-HydroxybenzoateHCID 1982125-Acetylsalicylamide

Product 1

HCID 222545695-Acetyl-2-((4-((2-aminoquinolin-8-yl)oxy)pentyl)oxy)benzamide

Procedure

The title compound was prepared according to the procedure described in Example 92 substituting 5-acetyl-2-hydroxybenzamide for methyl 3-hydroxybenzoate. 1H NMR (500 MHz, CDCl3) δ ppm 8.66 (d, 1H), 8.06 (dd, 1H), 7.96 (d, 1H), 7.32 (t, 1H), 7.22 (m, 1H), 7.12 (d, 1H), 7.04 (d, 1H), 6.97 (d, 1H), 4.71 (m, 1H), 4.38 (m, 1H), 4.26 (m, 1H), 2.58 (s, 3H), 2.24 (m, 2H), 1.92–2.13 (m, 2H), 1.48 (d, 3H); MS (DCI/NH3) m/z 408 [M+H]+.

Sources & evidence

ORD record
ord-e0aaa191442044858e50e227458c5e61
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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