p-Fluorophenethylamine → HCID 59730332, compound

HRID 130866Notes

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

Participants

Reactant 2

HCID 4653p-Fluorophenethylamine

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

Product 1

HCID 59730332HCID 59730332, compoundYield 94.9%

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 4-fluorophenethylamine (0.0256 g, 0.184 mmol) gives the title compound (0.0689 g. 94.9%): TOF MS ES+ 396.2 (M+H)+, HRMS calcd for C22H23N3O3F 396.1723 (M+H)+found 396.1714, time 0.41 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=7.1 min, 100% purity.

Sources & evidence

ORD record: ord-bdd15cd0bb3d4f8cb3350cfe70b4874a
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381719B2

Reaction notes

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