2-(3-Methylphenyl)ethan-1-amine → 5-{2-Fluoro-4-[(2-m-tolylethylamino)methyl]phenoxy}pyridine-2-carboxamide

HRID 228294Notes

Reaction equation

HRID 228294 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1.[CH3:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[CH2:24][CH2:25][NH2:26]>>[F:1][C:2]1[CH:17]=[C:16]([CH2:18][NH:26][CH2:25][CH2:24][C:23]2[CH:22]=[C:21]([CH3:20])[CH:29]=[CH:28][CH:27]=2)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1

Participants

3

Reactant 2

HCID 4100852-(3-Methylphenyl)ethan-1-amineHCID 597299375-(2-Fluoro-4-formylphenoxy)pyridine-2-carboxamide

Product 1

HCID 597302295-{2-Fluoro-4-[(2-m-tolylethylamino)methyl]phenoxy}pyridine-2-carboxamideYield 52.5%

Procedure

Using a method similar to Example 405, using 5-(2-fluoro-4-formylphenoxy)pyridine-2-carboxamide (Example 405, Part B) (0.040 g, 0.154 mmol) and 3-methylphenethylamine (0.021 g, 0.154 mmol) gives the title compound (0.0306 g, 52.5%): TOF MS ES+ 380.2 (M+H)+, HRMS calcd for C21H23N3O2F 380.1774 (M+H)+, found 380.1757, time 0.39 min; HPLC [YMC-Pack Pro C-18 (150×4.6 m, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 20-99% over 23 min], tR=8.4 min, 100% purity.

Sources & evidence

ORD record
ord-98fb9f88692b466e853b2f7384d2c00c
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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