Benzoyl chloride → HCID 11359309, compound

To a mixture of 6-aminomethyl-benzo[b]thiophene-2-carboxylic acid ethyl ester, hydrochloride salt (109 mg, 0.40 mmol), NMM (132 μL, 1.20 mmol) an DMAP (10 mg, 0.08 mmol) in anhydrous THF (5 mL) were added benzoyl chloride (55.7 μL, 0.48 mmol) and DMF (2.0 mL). After the reaction was complete, the reaction mixture was concentrated. To the residue were added MeOH (1 mL) and water (10 mL). The solid formed was filtered, washed with water and dried. This solid residue was dissolved in anhydrous MeOH (5 mL) and hydroxylamine hydrochloride (106 mg, 1.52 mmol) was added, followed by the addition of NaOMe solution (4.37 M in MeOH, 0.70 mL, 3.1 mmol). The mixture was allowed to stir at rt till the reaction was complete. The reaction mixture was concentrated and the residue was dissolved in a minimal amount of water. The obtained solution was acidified with 2N HCl to pH≈8. The solid formed was filtered, washed with water, collected and purified by flash column chromatography to give 6-(benzoylamino-methyl)-benzo[b]thiophene-2-carboxylic acid hydroxyamide as a white solid. 1H NMR (DMSO-d6, 200 MHz) δ 11.44 (brs, 1H), 9.27 (brs, 1H), 9.13 (t, J=6.2 Hz, 1H), 8.00-7.78 (m, 5H), 7.58-7.28 (m, 4H), 4.60 (d, J=5.8 Hz, 2H). MS (EI): cal'd 327.1 (MH+), exp 327.1 (MH+).

1. concentrationthe reaction mixture was concentrated
2. additionTo the residue were added MeOH (1 mL) and water (10 mL)
3. customThe solid formed
4. filtrationwas filtered
5. washwashed with water
6. customdried
7. dissolutionThis solid residue was dissolved in anhydrous MeOH (5 mL)
8. concentrationThe reaction mixture was concentrated
9. dissolutionthe residue was dissolved in a minimal amount of water
10. customThe solid formed
11. filtrationwas filtered
12. washwashed with water
13. customcollected
14. custompurified by flash column chromatography

ORD record

ord-7bdd23973e994c6a84f3bdb24d9403f9

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935724B2