Benzo[b]thiophene-3-ethanamine → 5-{4-[(2-Benzo[b]thiophen-3-ylethylamino)methyl]phenoxy}pyridine-2-carboxamide

HRID 130856

Reaction equation

HRID 130856 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH2:16])=[O:15])=[N:12][CH:13]=2)=[CH:5][CH:4]=1)=O.[S:19]1[CH:23]=[C:22]([CH2:24][CH2:25][NH2:26])[C:21]2[CH:27]=[CH:28][CH:29]=[CH:30][C:20]1=2>>[S:19]1[CH:23]=[C:22]([CH2:24][CH2:25][NH:26][CH2:1][C:3]2[CH:18]=[CH:17][C:6]([O:7][C:8]3[CH:9]=[CH:10][C:11]([C:14]([NH2:16])=[O:15])=[N:12][CH:13]=3)=[CH:5][CH:4]=2)[C:21]2[CH:27]=[CH:28][CH:29]=[CH:30][C:20]1=2

Participants

3

Reactant 2

HCID 26743Benzo[b]thiophene-3-ethanamineHCID 597301445-(4-Formylphenoxy)pyridine-2-carboxamide

Product 1

HCID 597303535-{4-[(2-Benzo[b]thiophen-3-ylethylamino)methyl]phenoxy}pyridine-2-carboxamideYield 50.2%

Procedure

Using a method similar to Example 405, a reaction of 5-(4-formylphenoxy)pyridine-2-carboxamide (Example 388, Part D) (0.0366 g, 0.151 mmol) and 2-benzo[b]thiophen-3-ylethylamine (0.0295 g, 0.166 mmol) gives the title compound (0.0306 g, 50.2%): TOF MS ES+ 404.1 (M+H)+, HRMS calcd for C23H22N3O2S 404.1433 (M+H)+, found 404.1423, 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=8.9 min. 100% purity.

Sources & evidence

ORD record
ord-0cc1dacef795437eba6205067c29d1f9
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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