Methylamine → Methyl-thieno[3,2-c]pyridin-2-ylmethyl-amine

Temperature

0 °C

A solution of thieno[3,2-c]pyridine-2-carbaldehyde (720 mg, 4.41 mmol) in a 2.0 M solution of methylamine in methanol (25 mL) was stirred at room temperature for S hours. After this time, the mixture was concentrated to dryness, dissolved in anhydrous methanol (10 mL) then cooled to 0° C. To this solution was added NaBH4 (167 mg, 4.41 mmol) in one portion. The mixture was allowed to warm to room temperature and stirred at this temperature overnight. The mixture was concentrated, dissolved in CH2Cl2 (100 mL) and treated with 1.0 N NaOH (20 mL). The aqueous layer was extracted with CH2Cl2 (2×20 mL). The combined organic fractions were washed with brine, dried over Na2SO4 then concentrated to give a yellow residue which was subjected to flash chromatography on silica gel (10% 2M NH3 in MeOH:CH2Cl2). The title compound was obtained as a white solid in 63.6% yield: 1H-NMR (300 MHz, CDCl3) δ 9.01 (s, 1H), 8.45 (d, J=5.5 Hz, 1H), 7.76 (d, J=5.5 Hz, 1H), 7.29 (s, 1H), 4.10 (s, 2H), 2.54 (s, 3H); MS (ES) m/e 179 (M+H)+.

1. concentrationAfter this time, the mixture was concentrated to dryness
2. dissolutiondissolved in anhydrous methanol (10 mL)
3. temperatureto warm to room temperature
4. concentrationThe mixture was concentrated
5. dissolutiondissolved in CH2Cl2 (100 mL)
6. additiontreated with 1.0 N NaOH (20 mL)
7. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
8. washThe combined organic fractions were washed with brine
9. dry with materialdried over Na2SO4
10. concentrationthen concentrated
11. customto give a yellow residue which

ORD record

ord-b3e490ded0ef4f68a7e4c3999b274f50

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790709B2