2-Methylphenethylamine → 6-{2-Methoxy-4-[(2-o-tolylethylamino)methyl]phenoxy}nicotinamide

HRID 130859Notes

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.[CH3:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[CH2:24][CH2:25][NH2:26]>>[CH3:20][O:19][C:5]1[CH:4]=[C:3]([CH2:1][NH:26][CH2:25][CH2:24][C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[CH3:21])[CH:18]=[CH:17][C:6]=1[O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=1

Participants

Reactant 2

HCID 20638682-Methylphenethylamine

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

Product 1

HCID 597303116-{2-Methoxy-4-[(2-o-tolylethylamino)methyl]phenoxy}nicotinamideYield 81.2%

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 2-methylphenethylamine (0.0248 g, 0.184 mmol) gives the title compound (0.0584 g. 81.2%): TOF MS ES+ 392.2 (M+H)+, HRMS calcd for C23H26N3O3 392.1974 (M+H)+, found 392.1966, 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=7.5 min, 97.6% purity.

Sources & evidence

ORD record: ord-c48ba745dcad43f8bb54ee28d2cf29e2
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381719B2

Reaction notes

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