Butylamine → 6-(4-Butylaminomethyl-2-methoxyphenoxy)nicotinamide

HRID 130862Notes

Reaction equation

HRID 130862 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)=[C:5]([O:19][CH3:20])[CH:4]=1)=O.[CH2:21]([NH2:25])[CH2:22][CH2:23][CH3:24]>>[CH2:21]([NH:25][CH2:1][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)=[C:5]([O:19][CH3:20])[CH:4]=1)[CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 597300166-(4-Formyl-2-methoxyphenoxy)nicotinamide

Product 1

HCID 597301866-(4-Butylaminomethyl-2-methoxyphenoxy)nicotinamideYield 75.7%

Procedure

Using a method similar to Example 405, a reaction of 6-(4-formyl-2-methoxyphenoxy)nicotinamide (Example 414, Part B) (0.050 g, 0.184 mmol) and n-butylamine (0.0134 g, 0.184 mmol) gives the title compound (0.0458 g, 75.7%): TOF MS ES+ 330.2 (M+H)+, HRMS calcd for C18H24N3O3 330.1818 (M+H)+, found 330.1802, time 0.39 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 20-99% over 23 min], tR=4.9 min, 100% purity.

Sources & evidence

ORD record
ord-be367757d07f4dc19fd2d8c18ddd938f
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

Loading…